3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid (2-amino-ethyl)-amide → 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid [2-amino-1-(3-fluoro-phenyl)-ethyl]-amide

HRID 570480Notes

Reaction equation

HRID 570480 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[S:8][CH:9]=[CH:10][C:11]=1[NH:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]2[NH:19][CH:20]=[CH:21][C:14]=12)=[O:6].NC([C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=1)CNC(=O)OC(C)(C)C.N1CCC[C@@H]1CNC(C1SC=CC=1NC1C=CN=C2NC=CC=12)=O>>[NH2:1][CH2:2][CH:3]([NH:4][C:5]([C:7]1[S:8][CH:9]=[CH:10][C:11]=1[NH:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]2[NH:19][CH:20]=[CH:21][C:14]=12)=[O:6])[C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=1

Participants

4

Reactant 3

HCID 509244533-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid (2-amino-ethyl)-amideHCID 669575583-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid ((R)-1-pyrrolidin-2-ylmethyl)-amideHCID 76853774Tert-butyl 2-amino-2-(3-fluorophenyl)ethylcarbamate

Product 1

HCID 509251973-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid [2-amino-1-(3-fluoro-phenyl)-ethyl]-amide

Procedure

This compound was prepared in an analogous manner as 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid (2-amino-ethyl)-amide using tert-butyl [2-amino-2-(3-fluorophenyl)ethyl]carbamate instead of tert-butyl-2-amino ethyl carbamate. LCMS (ESI) 496 (M+H) followed by deprotection in an analogous manner as 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid ((R)-1-pyrrolidin-2-ylmethyl)-amide. LCMS (ESI) 396 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 12.42 (1H, br. s.) 10.87 (1H, s) 9.24 (1H, d, J=8.59 Hz) 8.20 (1H, br. s.) 8.01 (1H, d, J=6.78 Hz) 7.95 (1H, d, J=5.22 Hz) 7.41 (1H, dd, J=3.51, 2.59 Hz) 7.32 (1H, d, J=5.22 Hz) 7.18-7.27 (1H, m) 7.13-7.17 (1H, m) 7.10 (1H, dd, J=12.89, 1.61 Hz) 7.04 (1H, td, J=8.90, 3.29 Hz) 6.94 (1H, br. s.) 6.58 (1H, d, J=6.93 Hz) 5.32 (1H, dd, J=18.28, 4.32 Hz) 3.18 (1H, dd, J=11.86, 5.12 Hz)

Sources & evidence

ORD record
ord-a831f1000940430ea365c23ed1edf676
Source dataset
uspto-grants-2015_05
Patent number
US09023847B2

Reaction notes

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