3-Thiophenecarboxaldehyde → 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid {2-[(thiophen-3-ylmethyl)-amino]-ethyl}-amide

HRID 570429Notes

Reaction equation

HRID 570429 reaction equation
COC1C=[CH:29][C:6]([CH2:7][NH:8][CH2:9][CH2:10][NH:11][C:12]([C:14]2[S:15][CH:16]=[CH:17][C:18]=2[NH:19][C:20]2[CH:25]=[CH:24][N:23]=[C:22]3[NH:26][CH:27]=[CH:28][C:21]=23)=[O:13])=[CH:5][CH:4]=1.[S:31]1C=CC(C=O)=C1>>[S:31]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][CH2:9][CH2:10][NH:11][C:12]([C:14]2[S:15][CH:16]=[CH:17][C:18]=2[NH:19][C:20]2[CH:25]=[CH:24][N:23]=[C:22]3[NH:26][CH:27]=[CH:28][C:21]=23)=[O:13])=[CH:29]1

Participants

3

Reactant 2

HCID 681353-ThiophenecarboxaldehydeHCID 509244513-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid [2-(4-methoxy-benzylamino)-ethyl]-amide

Product 1

HCID 509244553-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid {2-[(thiophen-3-ylmethyl)-amino]-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-(4-methoxy-benzylamino)-ethyl]amide using 3-thiophenecarboxaldehyde instead of 4-methoxy benzaldehyde. LCMS (ESI) 398 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.52 (1H, br. s.) 10.26 (1H, s) 7.98-8.08 (2H, m) 7.77 (1H, d, J=5.42 Hz) 7.46 (1H, d, J=5.42 Hz) 7.42 (1H, dd, J=4.93, 2.98 Hz) 7.30 (1H, dd, J=3.29, 2.66 Hz) 7.24 (1H, dd, J=2.78, 1.03 Hz) 7.05 (1H, dd, J=4.91, 1.20 Hz) 6.80 (1H, d, J=5.42 Hz) 6.43 (1H, dd, J=3.44, 1.93 Hz) 3.67 (2H, s) 3.34 (2H, d, J=5.76 Hz) 2.64 (2H, t, J=6.54 Hz)

Sources & evidence

ORD record
ord-438ce5f4738947b3a1a69ee7b818fa27
Source dataset
uspto-grants-2015_05
Patent number
US09023847B2

Reaction notes

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