p-Bromophenethylamine → 3-(7H-Pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carboxylic acid [2-(4-bromo-phenyl)-ethyl]-amide

HRID 570504Notes

Reaction equation

HRID 570504 reaction equation
[CH2:1]([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.[Br:26][C:27]1[CH:35]=[CH:34][C:30]([CH2:31]CN)=[CH:29][CH:28]=1>>[Br:26][C:27]1[CH:35]=[CH:34][C:30]([CH2:31][CH2:1][NH:8][C:9]([C:11]2[S:12][CH:13]=[CH:14][C:15]=2[NH:16][C:17]2[C:18]3[CH:25]=[CH:24][NH:23][C:19]=3[N:20]=[CH:21][N:22]=2)=[O:10])=[CH:29][CH:28]=1

Participants

3

Reactant 2

HCID 533915p-BromophenethylamineHCID 509238613-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carboxylic acid benzylamide

Product 1

HCID 509238603-(7H-Pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carboxylic acid [2-(4-bromo-phenyl)-ethyl]-amideYield 20%

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 4-bromophenethylamine instead of benzylamine and obtained in 20% yield (HPLC: 60%, RT: 6.81 min). 1H NMR (DMSO-d6) 11.98 (br s, 1H), 11.37 (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), 7.50-7.47 (m, 2H), 7.37 (dd, J=3.3, 2.2 Hz, 1H), 7.25-7.21 (m, 2H), 6.45 (dd, J=3.6, 1.8 Hz, 1H), 3.54-3.47 (m, 2H), 2.85 (t, J=7.0 Hz, 2H); MS (m/z) 442 [M+H]+.

Workup

  1. customobtained in 20% yield (HPLC: 60%, RT: 6.81 min)

Sources & evidence

ORD record
ord-7d7c122207bb4da0aaf7876dd2d27b9c
Source dataset
uspto-grants-2015_05
Patent number
US09023847B2

Reaction notes

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