1-[(1R)-1-chloroethyl]-3-(methylsulfonyl)benzene → (2R)-2-{[2-Amino-5-({(1S)-1-[3-(methylsulfonyl)phenyl]ethyl}thio)[1,3]thiazolo[4,5-d]pyrimidin-7-yl]-amino}-4-methylpentan-1-ol

HRID 60521Notes

Reaction equation

HRID 60521 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:9]([NH:10][C@H:11]([CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:12][OH:13])=[N:8][C:7]([SH:18])=[N:6][C:5]=2[N:19]=1.Cl[C@@H:21]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([S:29]([CH3:32])(=[O:31])=[O:30])[CH:24]=1)[CH3:22]>>[NH2:1][C:2]1[S:3][C:4]2[C:9]([NH:10][C@H:11]([CH2:14][CH:15]([CH3:16])[CH3:17])[CH2:12][OH:13])=[N:8][C:7]([S:18][C@H:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([S:29]([CH3:32])(=[O:30])=[O:31])[CH:24]=3)[CH3:22])=[N:6][C:5]=2[N:19]=1

Participants

3

Reactant 2

HCID 666227131-[(1R)-1-chloroethyl]-3-(methylsulfonyl)benzeneHCID 178445911HCID 178445911, compound

Product 1

HCID 11964579(2R)-2-{[2-Amino-5-({(1S)-1-[3-(methylsulfonyl)phenyl]ethyl}thio)[1,3]thiazolo[4,5-d]pyrimidin-7-yl]-amino}-4-methylpentan-1-ol

Procedure

The title compound was prepared from (2R)-2-[(2-amino-5-mercapto[1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]-4-methylpentan-1-ol (16.5 g, 55.3 mmol) and 1-[(1R)-1-chloroethyl]-3-(methylsulfonyl)benzene (12.1 g, 55.3 mmol) according to general method A.

Sources & evidence

ORD record
ord-130492fc759249a48e39d6f8cc38a098
Source dataset
uspto-grants-2016_09
Patent number
US09440992B2

Reaction notes

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