1-BOC-3-Aminopiperidine → 3-{[2-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-3-carbonyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester
Reaction equation
C(OC(N1CCC(NC(C2SC=CC=2NC2C=CN=C3NC=CC=23)=O)C1)=O)(C)(C)C.[C:31]([N:38]1[CH2:43][CH2:42][CH2:41][CH:40]([NH2:44])[CH2:39]1)([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32].[NH:45]1[C:49]2=[N:50][CH:51]=[CH:52][C:53]([NH:54][C:55]3[S:56][CH:57]=[CH:58][C:59]=3[C:60](O)=[O:61])=[C:48]2[CH:47]=[CH:46]1>>[C:34]([O:33][C:31]([N:38]1[CH2:43][CH2:42][CH2:41][CH:40]([NH:44][C:60]([C:59]2[CH:58]=[CH:57][S:56][C:55]=2[NH:54][C:53]2[CH:52]=[CH:51][N:50]=[C:49]3[NH:45][CH:46]=[CH:47][C:48]=23)=[O:61])[CH2:39]1)=[O:32])([CH3:37])([CH3:36])[CH3:35]Participants
Reactant 3
Product 1
Procedure
This compound was prepared in an analogous manner as 3-{[3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carbonyl]-amino}-pyrrolidine-1-carboxylic acid tert-butyl ester using 1-BOC-3-aminopiperidine instead of 1-BOC-3-aminopyrrolidine and 2-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-3-carboxylic acid instead of 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid. LCMS (ESI) 442 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.90 (1H, br. s.) 11.64 (1H, s) 8.13 (1H, d, J=5.42 Hz) 7.99 (1H, d, J=6.30 Hz) 7.53 (1H, d, J=5.91 Hz) 7.35 (1H, dd, J=3.44, 2.46 Hz) 6.96 (1H, d, J=5.42 Hz) 6.90 (1H, d, J=5.81 Hz) 6.44 (1H, dd, J=3.47, 2.00 Hz) 3.82 (1H, td, J=8.59, 4.93 Hz) 2.78 (1H, br. s.) 1.82-1.94 (1H, m) 1.66-1.77 (1H, m) 1.53 (1H, d, J=11.42 Hz) 1.31-1.45 (10H, m)
Sources & evidence
- ORD record
- ord-35feb3f6bfdd4d6fa2dfe26b5c8b8cb6
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09023847B2
Reaction notes
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