Benzenemethanamine, 3-chloro- → 3-(7H-Pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carboxylic acid 3-chloro-benzylamide

HRID 570495Notes

Reaction equation

HRID 570495 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])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:26]C1C=C(C=CC=1)CN>>[Cl:26][C:6]1[CH:7]=[C:2]([CH:3]=[CH:4][CH:5]=1)[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]

Participants

3

Reactant 2

HCID 77802Benzenemethanamine, 3-chloro-HCID 509238613-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carboxylic acid benzylamide

Product 1

HCID 669578613-(7H-Pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carboxylic acid 3-chloro-benzylamideYield 15%

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-chlorobenzylamine instead of benzylamine and obtained in 15% yield (HPLC: 94%, RT: 6.54 min). 1H NMR (DMSO-d6) 11.98 (br s, 1H), 11.33 (s, 1H), 8.61 (t, J=6.0 Hz, 1H), 8.50 (d, J=5.5 Hz, 1H), 8.39 (s, 1H), 7.81 (d, J=5.5 Hz, 1H), 7.41-7.29 (m, 5H), 6.43 (dd, J=3.7, 1.8 Hz, 1H), 4.50 (d, J=5.9 Hz, 2H); MS (m/z) 384 [M+H]+ (35Cl).

Workup

  1. customobtained in 15% yield (HPLC: 94%, RT: 6.54 min)

Sources & evidence

ORD record
ord-5af319cdb9504ce4903c7cc8ea128c01
Source dataset
uspto-grants-2015_05
Patent number
US09023847B2

Reaction notes

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