3-[(1R)-1-chloroethyl]benzonitrile → 3-{(1S)-1-[(2-Amino-7-{[(1R)-1-(hydroxymethyl)-3-methylbutyl]amino}[1,3]thiazolo[4,5-d]pyrimidin-5-yl)thio]ethyl}benzonitrile

HRID 60522Notes

Reaction equation

HRID 60522 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:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[C:26]#[N:27])[CH3:22]>>[NH2:1][C:2]1[S:3][C:4]2[C:9]([NH:10][C@@H:11]([CH2:12][OH:13])[CH2:14][CH:15]([CH3:16])[CH3:17])=[N:8][C:7]([S:18][C@H:21]([C:23]3[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=3)[C:26]#[N:27])[CH3:22])=[N:6][C:5]=2[N:19]=1

Participants

3

Reactant 2

HCID 666231523-[(1R)-1-chloroethyl]benzonitrileHCID 178445911HCID 178445911, compound

Product 1

HCID 582304083-{(1S)-1-[(2-Amino-7-{[(1R)-1-(hydroxymethyl)-3-methylbutyl]amino}[1,3]thiazolo[4,5-d]pyrimidin-5-yl)thio]ethyl}benzonitrileYield 31%

Procedure

The title compound was prepared in 31% yield from (2R)-2-[(2-amino-5-mercapto[1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]-4-methylpentan-1-ol (200 mg, 0.67 mmol) and 3-[(1R)-1-chloroethyl]benzonitrile (166 mg, 1.0 mmol) according to general method A.

Sources & evidence

ORD record
ord-116e4958e67447e994600c2c0a3082ac
Source dataset
uspto-grants-2016_09
Patent number
US09440992B2

Reaction notes

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