2-Amino-5-cyanopyridine → (2S)-3-[2-(tert-butyl-dimethylsilyl)oxyethoxy]-N-(5-cyanopyridin-2-yl)-2-[1-(3-fluoro-2-methylphenyl)pyrazolo[4,5-e]pyrimidin-4-yl]oxypropanamide

HRID 1098182Notes

Reaction equation

HRID 1098182 reaction equation
CO[C:3](=[O:45])[C@@H:4]([O:27][C:28]1[N:33]=[CH:32][N:31]=[C:30]2[N:34]([C:37]3[CH:42]=[CH:41][CH:40]=[C:39]([F:43])[C:38]=3[CH3:44])[N:35]=[CH:36][C:29]=12)[CH2:5][O:6][CH2:7][CH2:8][O:9][Si:10]([C:23]([CH3:26])([CH3:25])[CH3:24])([C:17]1C=CC=CC=1)[C:11]1C=CC=CC=1.[NH2:46][C:47]1[CH:54]=[CH:53][C:50]([C:51]#[N:52])=[CH:49][N:48]=1>>[Si:10]([O:9][CH2:8][CH2:7][O:6][CH2:5][C@H:4]([O:27][C:28]1[C:29]2[CH:36]=[N:35][N:34]([C:37]3[CH:42]=[CH:41][CH:40]=[C:39]([F:43])[C:38]=3[CH3:44])[C:30]=2[N:31]=[CH:32][N:33]=1)[C:3]([NH:46][C:47]1[CH:54]=[CH:53][C:50]([C:51]#[N:52])=[CH:49][N:48]=1)=[O:45])([C:23]([CH3:24])([CH3:25])[CH3:26])([CH3:11])[CH3:17]

Participants

3

Reactant 2

HCID 8182602-Amino-5-cyanopyridineHCID 59279546(2S)-methyl 3-(2-(tert-butyldiphenylsilyloxy)ethoxy)-2-(1-(3-fluoro-2-methylphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)propanoate

Product 1

HCID 57504655(2S)-3-[2-(tert-butyl-dimethylsilyl)oxyethoxy]-N-(5-cyanopyridin-2-yl)-2-[1-(3-fluoro-2-methylphenyl)pyrazolo[4,5-e]pyrimidin-4-yl]oxypropanamide

Procedure

Prepared using a procedure analogous to that described for Intermediate AE1 using (2S)-methyl-3-(2-(tert-butyldiphenylsilyloxy)ethoxy)-2-(1-(3-fluoro-2-methylphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)propanoate (Intermediate AF4) and 6-aminonicotinonitrile. 1H NMR (400 MHz, DMSO) d 0.89 (9H, s), 1.96 (3H, d), 3.83-3.69 (4H, m), 4.12-4.04 (1H, m), 4.17 (1H, dd), 6.02 (1H, m), 7.51-7.27 (9H, m), 7.60 (4H, m), 8.13 (1H, d), 8.22 (1H, dd), 8.51 (1H, s), 8.55 (1H, s), 8.81 (1H, d), 11.56 (1H, s). m/z (ES+) (M+H)+=716; HPLC tR=3.29 min.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-c4c191825fb24305bf8e29593e4cca94
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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