2-Amino-5-chloropyridine → (2S)-3-[2-(tert-butyl-dimethylsilyl)oxyethoxy]-2-[1-(2-chlorophenyl)pyrazolo[4,5-e]pyrimidin-4-yl]oxy-N-(5-chloropyridin-2-yl)propanamide
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]=[CH:40][C:39]=3[Cl:44])[N:36]=[CH:37][C:30]=12)[C:24]([O:26]C)=O)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1C=CC=CC=1)[C:2]1C=CC=CC=1.[Cl:45][C:46]1[CH:47]=[CH:48][C:49]([NH2:52])=[N:50][CH:51]=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]=[CH:40][C:39]=3[Cl:44])[C:31]=2[N:32]=[CH:33][N:34]=1)[C:24]([NH:52][C:49]1[CH:48]=[CH:47][C:46]([Cl:45])=[CH:51][N:50]=1)=[O:26])([C:14]([CH3:15])([CH3:17])[CH3:16])([CH3:8])[CH3:2]Participants
3
Reactant 2
Product 1
Procedure
Prepared from (2S)-methyl 3-(2-(tert-butyldiphenylsilyloxy)ethoxy)-2-(1-(2-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)propanoate (Intermediate AG2) (950 mg, 1.51 mmol) according to the method for Intermediate AE3 using 5-chloropyridin-2-amine. 1H NMR (400 MHz, DMSO) δ 0.88 (9H, s), 3.71-3.84 (4H, m), 4.02-4.07 (1H, m), 4.13-4.18 (1H, m), 5.97-5.99 (1H, m), 7.34-7.43 (6H, m), 7.56-7.67 (7H, m), 7.74-7.77 (1H, m), 7.86-7.89 (1H, m), 8.00-8.03 (1H, m), 8.40-8.41 (1H, m), 8.52 (1H, s), 8.57 (1H, s), 11.25 (1H, s); m/z (ESI+) (M+H)+=727; HPLC tR=3.49 min.
Sources & evidence
- ORD record
- ord-b3b5017fcd394694b32577beb33c376a
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08143263B2
Reaction notes
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