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CAS 196929-78-9

(R)-2-methylpropane-2-sulfinamide(R)-(+)-2-Methyl-2-propanesulfinamide(+)-(R)-2-Methylpropane-2-sulfinamide

Codes: APER-021, (XX)1024528-1-b, IXAB-052, SILO-055, (XVI)989842-2-b

Application context (from source-drug indications)

Plaque psoriasisApremilastBehçet's syndromeApremilastOral ulcerApremilastPsoriasisApremilastPsoriatic arthritisApremilastNon-small cell lung cancerPralsetinibThyroid cancerPralsetinibMedullary thyroid cancerPralsetinibBreast cancerIxabepiloneMetastatic breast cancerIxabepiloneCervical cancerIxabepiloneProstate cancerIxabepiloneSolid tumourIxabepiloneNeutropeniaIxabepiloneBenign prostatic hyperplasiaSilodosinLower urinary tract symptomsSilodosinUrolithiasisSilodosinKidney stonesSilodosinContraceptive useSilodosinUrinary tract stonesSilodosinPlaque psoriasisMufemilastUlcerative colitisMufemilastBehçet's syndromeMufemilastPsoriasisMufemilastChronic obstructive pulmonary diseaseMufemilastAtopic dermatitisMufemilast

Source drugs (routes using this intermediate)

DrugTierExpiry
ApremilastTier B — Position early2028
PralsetinibTier C — Watch / trade2031
IxabepiloneTier C — Watch / trade-
SilodosinTier C — Watch / trade-
MufemilastTier C — Watch / trade-

Position in synthesis routes (up/downstream chain)

Ordered by route registration; left → right is the synthesis direction. The highlighted node is the current CAS; others link to their own profiles.

IxabepiloneOptimised routesteps: 10total yield: 27 mg
tert-butyl (S,E)-(2-methyl-1-(2-methylthiazol-4-yl)-5-oxopent-1-en-3-yl)carbamate→(S,1E,5Z)-6-iodo-2-methyl-1-(2-methylthiazol-4-yl)hepta-1,5-dien-3-amine→(4S,7R,8S,9S,16S,Z)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)azacyclohexadec-13-ene-2,6-dione→1-((3aR,6R,7aS)-2,2-dioxidotetrahydro-3H-3a,6-methanobenzo[c]isothiazol-1(4H)-yl)ethan-1-one compound with ethane (1:1)→3,3-dimethylhexane-2,4-dione→(S)-1-((3aR,6R,7aS)-2,2-dioxidotetrahydro-3H-3a,6-methanobenzo[c]isothiazol-1(4H)-yl)-3-hydroxy-4,4-dimethylheptane-1,5-dione compound with ethane (1:1)→(S)-3-((tert-butyldimethylsilyl)oxy)-1-((3aR,6R,7aS)-2,2-dioxidotetrahydro-3H-3a,6-methanobenzo[c]isothiazol-1(4H)-yl)-4,4-dimethylheptane-1,5-dione compound with ethane (1:1)→(S)-2-methylpent-4-enal→(3S,6R,7S,8S)-3-((tert-butyldimethylsilyl)oxy)-1-((3aR,6R,7aS)-2,2-dioxidotetrahydro-3H-3a,6-methanobenzo[c]isothiazol-1(4H)-yl)-7-hydroxy-4,4,6,8-tetramethylundec-10-ene-1,5-dione compound with ethane (1:1)→(3S,6R,7S,8S)-3,7-bis((tert-butyldimethylsilyl)oxy)-1-((3aR,6R,7aS)-2,2-dioxidotetrahydro-3H-3a,6-methanobenzo[c]isothiazol-1(4H)-yl)-4,4,6,8-tetramethylundec-10-ene-1,5-dione compound with ethane (1:1)→tert-butyl ((S,1E,5Z)-6-iodo-2-methyl-1-(2-methylthiazol-4-yl)hepta-1,5-dien-3-yl)carbamate→tert-butyl ((1E,3S,5Z,10S,11S,12R,15S)-11,15-bis((tert-butyldimethylsilyl)oxy)-17-((3aR,6R,7aS)-2,2-dioxidotetrahydro-3H-3a,6-methanobenzo[c]isothiazol-1(4H)-yl)-2,6,10,12,14,14-hexamethyl-1-(2-methylthiazol-4-yl)-13,17-dioxoheptadeca-1,5-dien-3-yl)carbamate compound with ethane (1:1)→(3S,6R,7S,8S,12Z,15S,16E)-15-((tert-butoxycarbonyl)amino)-3,7-bis((tert-butyldimethylsilyl)oxy)-4,4,6,8,12,16-hexamethyl-17-(2-methylthiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid→(3S,6R,7S,8S,12Z,15S,16E)-15-amino-3,7-bis((tert-butyldimethylsilyl)oxy)-4,4,6,8,12,16-hexamethyl-17-(2-methylthiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid→(4S,7R,8S,9S,16S,Z)-4,8-bis((tert-butyldimethylsilyl)oxy)-5,5,7,9,13-pentamethyl-16-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)azacyclohexadec-13-ene-2,6-dione→(E)-2-methyl-3-(2-methylthiazol-4-yl)acrylaldehyde→(R)-2-methylpropane-2-sulfinamide→(R)-2-methyl-N-((1E,2E)-2-methyl-3-(2-methylthiazol-4-yl)allylidene)propane-2-sulfinamide→3-bromoprop-1-ene→(R)-2-methyl-N-((S,E)-2-methyl-1-(2-methylthiazol-4-yl)hexa-1,5-dien-3-yl)propane-2-sulfinamide→(S,E)-2-methyl-1-(2-methylthiazol-4-yl)hexa-1,5-dien-3-amine→tert-butyl (S,E)-(2-methyl-1-(2-methylthiazol-4-yl)hexa-1,5-dien-3-yl)carbamate→tert-butyl ((3S,E)-5,6-dihydroxy-2-methyl-1-(2-methylthiazol-4-yl)hex-1-en-3-yl)carbamate

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