3-{[2-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-3-carbonyl]-amino}-pyrrolidine-1-carboxylic acid tert-butyl ester → 2-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-3-carboxylic acid pyrrolidin-3-ylamide
Reaction equation
N1CCC[C@@H]1CNC(C1SC=CC=1NC1C=CN=C2NC=CC=12)=O.C(OC([N:32]1[CH2:36][CH2:35][CH:34]([NH:37][C:38]([C:40]2[CH:44]=[CH:43][S:42][C:41]=2[NH:45][C:46]2[CH:51]=[CH:50][N:49]=[C:48]3[NH:52][CH:53]=[CH:54][C:47]=23)=[O:39])[CH2:33]1)=O)(C)(C)C>>[NH:32]1[CH2:36][CH2:35][CH:34]([NH:37][C:38]([C:40]2[CH:44]=[CH:43][S:42][C:41]=2[NH:45][C:46]2[CH:51]=[CH:50][N:49]=[C:48]3[NH:52][CH:53]=[CH:54][C:47]=23)=[O:39])[CH2:33]1Participants
Reactant 2
Product 1
Procedure
This compound was prepared in an analogous manner as 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid ((R)-1-pyrrolidin-2-ylmethyl)-amide using 3-{[2-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-3-carbonyl]-amino}-pyrrolidine-1-carboxylic acid tert-butyl ester instead of (R)-2-({[3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carbonyl]-amino}methyl)pyrrolidine-1-carboxylic acid tert-butyl ester LCMS (ESI) 328 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 12.58 (1H, br. s.) 11.49 (1H, s) 8.89 (1H, d, J=6.93 Hz) 8.18 (1H, d, J=6.74 Hz) 7.67 (1H, d, J=5.86 Hz) 7.46 (1H, dd, J=3.32, 2.34 Hz) 7.42 (1H, d, J=5.86 Hz) 6.80 (1H, d, J=6.83 Hz) 6.76 (1H, dd, J=3.42, 1.56 Hz) 4.49 (1H, dt, J=6.66, 4.53 Hz) 3.33 (2H, dt, J=12.40, 6.30 Hz) 3.18 (2H, td, J=10.93, 6.44 Hz) 2.12 (1H, dd, J=13.42, 7.47 Hz) 1.84-2.00 (0H, m) 1.16-1.42 (1H, m)
Sources & evidence
- ORD record
- ord-db4421b5cab14c40872a4e3f48f7efb3
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09023847B2
Reaction notes
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