Phenethylamine → 3-(7H-Pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carboxylic acid phenethylamide

HRID 570496Notes

Reaction equation

HRID 570496 reaction equation
C([NH:8][C:9]([C:11]1[S:12][CH:13]=[CH:14][C:15]=1[NH:16][C:17]1[C:18]2[CH:25]=[CH:24][NH:23][C:19]=2[N:20]=[CH:21][N:22]=1)=[O:10])C1C=CC=CC=1.[CH2:26](N)[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[CH2:26]([NH:8][C:9]([C:11]1[S:12][CH:13]=[CH:14][C:15]=1[NH:16][C:17]1[C:18]2[CH:25]=[CH:24][NH:23][C:19]=2[N:20]=[CH:21][N:22]=1)=[O:10])[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

3

Reactant 2

HCID 1001PhenethylamineHCID 509238613-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carboxylic acid benzylamide

Product 1

HCID 509238573-(7H-Pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carboxylic acid phenethylamide

Procedure

The title compound was prepared in an analogous manner as 3-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carboxylic acid benzylamide using phenethylamine instead of benzylamine and obtained in 25% (HPLC: 90%, RT: 6.36 min). 1H NMR (DMSO-d6) 11.96 (br s, 1H), 11.38 (s, 1H), 8.47 (d, J=5.5 Hz, 1H), 8.38 (s, 1H), 8.32 (t, J=5.5 Hz, 1H), 7.75 (d, J=5.1 Hz, 1H), 7.36 (dd, J=3.7, 2.6 Hz, 1H), 7.33-7.18 (m, 5H), 6.46 (dd, J=3.7, 1.8 Hz, 1H), 3.54-3.47 (m, 2H), 2.87 (dd, J=8.1, 7.0 Hz, 2H); MS (m/z) 364 [M+H]+.

Workup

  1. customobtained in 25% (HPLC: 90%, RT: 6.36 min)

Sources & evidence

ORD record
ord-b22d963a3bc446238dbfcc851aa03a9b
Source dataset
uspto-grants-2015_05
Patent number
US09023847B2

Reaction notes

Loading…