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

HRID 1098184Notes

Reaction equation

HRID 1098184 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][O:21][CH2:22][C@H:23]([O:28][C:29]1[N:34]=[CH:33][N:32]=[C:31]2[N:35]([C:38]3[CH:43]=[CH:42][CH:41]=[C:40]([F:44])[C:39]=3[CH3:45])[N:36]=[CH:37][C:30]=12)[C:24](OC)=[O:25])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1C=CC=CC=1)[C:2]1C=CC=CC=1.[Cl:46][C:47]1[CH:48]=[CH:49][C:50]([NH2:53])=[N:51][CH:52]=1>>[Si:1]([O:18][CH2:19][CH2:20][O:21][CH2:22][C@H:23]([O:28][C:29]1[C:30]2[CH:37]=[N:36][N:35]([C:38]3[CH:43]=[CH:42][CH:41]=[C:40]([F:44])[C:39]=3[CH3:45])[C:31]=2[N:32]=[CH:33][N:34]=1)[C:24]([NH:53][C:50]1[CH:49]=[CH:48][C:47]([Cl:46])=[CH:52][N:51]=1)=[O:25])([C:14]([CH3:15])([CH3:16])[CH3:17])([CH3:8])[CH3:2]

Participants

3

Reactant 2

HCID 661742-Amino-5-chloropyridineHCID 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 57504660(2S)-3-[2-(tert-butyl-dimethylsilyl)oxyethoxy]-N-(5-chloropyridin-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 5-chloropyridin-2-amine. 1H NMR (400 MHz, DMSO) d 0.87 (9H, s), 1.96 (3H, d), 3.75 (4H, m), 4.10-4.02 (1H, m), 4.15 (1H, m), 6.00 (1H, m), 7.38 (9H, m), 7.63-7.57 (4H, m), 7.88 (1H, dd), 8.03 (1H, d), 8.40 (1H, d), 8.52 (1H, s), 8.56 (1H, s), 11.25 (1H, s).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-c63305d3a910405c9001e5eb97055987
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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