5-Methyl-3-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carboxylic acid methyl ester → 5-Methyl-3-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carboxylic acid 3-chloro-benzylamide

HRID 570502Notes

Reaction equation

HRID 570502 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[CH2:5][NH:6][C:7]([C:9]1[S:10][CH:11]=[CH:12][C:13]=1[NH:14][C:15]1[C:16]2[CH:23]=[CH:22][NH:21][C:17]=2[N:18]=[CH:19][N:20]=1)=[O:8].[CH3:27]OC(C1SC(C)=CC=1NC1C2C=CNC=2N=CN=1)=O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[CH2:5][NH:6][C:7]([C:9]1[S:10][C:11]([CH3:27])=[CH:12][C:13]=1[NH:14][C:15]1[C:16]2[CH:23]=[CH:22][NH:21][C:17]=2[N:18]=[CH:19][N:20]=1)=[O:8]

Participants

3

Reactant 2

HCID 669577805-Methyl-3-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carboxylic acid methyl esterHCID 669578613-(7H-Pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carboxylic acid 3-chloro-benzylamide

Product 1

HCID 509238555-Methyl-3-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carboxylic acid 3-chloro-benzylamideYield 50%

Procedure

The title compound was prepared in an analogous manner as 3-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carboxylic acid 3-chloro-benzylamide using 5-methyl-3-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carboxylic acid methyl ester instead of 3-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carboxylic acid methyl ester and obtained in 50% yield (HPLC: 98%, RT: 3.85 min). 1H NMR (DMSO-d6) 11.98 (br s, 1H), 11.39 (s, 1H), 8.68 (t, J=6.0 Hz, 1H), 8.39 (s, 1H), 8.28 (d, J=1.1 Hz, 1H), 7.40-7.28 (m, 5H), 6.41 (dd, J=3.3, 1.8 Hz, 1H), 4.48 (d, J=5.9 Hz, 2H), 2.55 (s, 3H); MS (m/z) 398 [M+H]+ (35Cl).

Workup

  1. customobtained in 50% yield (HPLC: 98%, RT: 3.85 min)

Sources & evidence

ORD record
ord-bf066d7d72bc463a9c59148d78a105b3
Source dataset
uspto-grants-2015_05
Patent number
US09023847B2

Reaction notes

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