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

HRID 570503Notes

Reaction equation

HRID 570503 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.[F:26][C:27]1[CH:35]=[CH:34][C:30]([CH2:31]CN)=[CH:29][CH:28]=1>>[F: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 4653p-FluorophenethylamineHCID 509238613-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carboxylic acid benzylamide

Product 1

HCID 509238593-(7H-Pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carboxylic acid [2-(4-fluoro-phenyl)-ethyl]-amideYield 14%

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-fluorophenethylamine instead of benzylamine and obtained in 14% yield (HPLC: 92%, RT: 6.36 min). 1H NMR (DMSO-d6) 11.97 (br s, 1H), 11.37 (s, 1H), 8.47 (d, J=5.4 Hz, 1H), 8.38 (s, 1H), 8.31 (t, J=5.7 Hz, 1H), 7.75 (d, J=5.4 Hz, 1H), 7.37 (dd, J=3.4, 2.4 Hz, 1H), 7.32-7.26 (m, 2H), 7.16-7.08 (m, 2H), 6.45 (dd, J=3.6, 1.9 Hz, 1H), 3.49 (dd, J=14.3, 6.4 Hz, 2H), 2.86 (t, J=7.6 Hz, 2H); MS (m/z) 382 [M+H]+.

Workup

  1. customobtained in 14% yield (HPLC: 92%, RT: 6.36 min)

Sources & evidence

ORD record
ord-0625223bc7d043dfb8a6e40e5b152b2b
Source dataset
uspto-grants-2015_05
Patent number
US09023847B2

Reaction notes

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