3-chloro-2-(4-chloro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)benzonitrile → (2S)-3-(2-(tert-butyldiphenylsilyloxy)ethoxy)-2-(1-(2-chloro-6-cyanophenyl)-1H-pyrazolo [3,4-d]pyrimidin-4-yloxy)-N-(5-methylpyridin-2-yl)propanamide

HRID 1098196Notes

Reaction equation

HRID 1098196 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][O:21][CH2:22][C@H:23]([OH:34])[C:24]([NH:26][C:27]1[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][N:28]=1)=[O:25])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:35][C:36]1[C:37]([N:44]2[C:48]3=[N:49][CH:50]=[N:51][C:52](Cl)=[C:47]3[CH:46]=[N:45]2)=[C:38]([CH:41]=[CH:42][CH:43]=1)[C:39]#[N:40]>>[Si:1]([O:18][CH2:19][CH2:20][O:21][CH2:22][C@H:23]([O:34][C:52]1[N:51]=[CH:50][N:49]=[C:48]2[N:44]([C:37]3[C:38]([C:39]#[N:40])=[CH:41][CH:42]=[CH:43][C:36]=3[Cl:35])[N:45]=[CH:46][C:47]=12)[C:24]([NH:26][C:27]1[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][N:28]=1)=[O:25])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 575045663-chloro-2-(4-chloro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)benzonitrileHCID 57504665(S)-3-(2-(tert-butyldiphenylsilyloxy)ethoxy)-2-hydroxy-N-(5-methylpyridin-2-yl)propanamide

Product 1

HCID 57504530(2S)-3-(2-(tert-butyldiphenylsilyloxy)ethoxy)-2-(1-(2-chloro-6-cyanophenyl)-1H-pyrazolo [3,4-d]pyrimidin-4-yloxy)-N-(5-methylpyridin-2-yl)propanamide

Procedure

Prepared using a procedure analogous to that described with Intermediate AH7 using (S)-3-(2-(tert-butyldiphenylsilyloxy)ethoxy)-N-(5-methylpyridin-2-yl)-2-hydroxypropanamide (Intermediate AU2) and 3-chloro-2-(4-chloro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)benzonitrile (Intermediate AH6). m/z (ES+) (M+H)+=732; HPLC tR=3.76 min

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-c9ae12fa4ba54f948e2f25f8a7b7c61f
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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