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

HRID 570506Notes

Reaction equation

HRID 570506 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.[Cl:26][C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][CH:35]=1)[CH2:30]CN>>[Cl:26][C:27]1[CH:28]=[C:29]([CH2:30][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:33]=[CH:34][CH:35]=1

Participants

3

Reactant 2

HCID 1393813-ChlorophenethylamineHCID 509238613-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carboxylic acid benzylamide

Product 1

HCID 509238583-(7H-Pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carboxylic acid [2-(3-chloro-phenyl)-ethyl]-amideYield 32%

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 3-chlorophenethylamine instead of benzylamine and obtained in 32% yield. 1H NMR (DMSO-d6) 11.98 (br s, 1H), 11.37 (s, 1H), 8.48 (d, J=5.5 Hz, 1H), 8.38 (s, 1H), 8.33 (t, J=5.5 Hz, 1H), 7.76 (d, J=5.5 Hz, 1H), 7.38-7.23 (m, 5H), 6.45 (dd, J=3.3, 1.8 Hz, 1H), 3.55-3.50 (m, 2H), 2.89 (t, J=7.5 Hz, 2H); MS (m/z) 398 [M+H]+.

Workup

  1. customobtained in 32% yield

Sources & evidence

ORD record
ord-5e2515a616e84f6e977ced63a097af05
Source dataset
uspto-grants-2015_05
Patent number
US09023847B2

Reaction notes

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