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

HRID 570499Notes

Reaction equation

HRID 570499 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]1S[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].C[O:28]C(C1OC=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[O:28][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]

Participants

3

Reactant 2

HCID 669577963-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-furan-2-carboxylic acid methyl esterHCID 669578613-(7H-Pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carboxylic acid 3-chloro-benzylamide

Product 1

HCID 669574393-(7H-Pyrrolo[2,3-d]pyrimidin-4-ylamino)-furan-2-carboxylic acid 3-chloro-benzylamideYield 9%

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 3-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-furan-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 9% yield. 1H NMR (DMSO-d6) 11.97 (br s, 1H), 9.67 (s, 1H), 9.01 (t, J=6.2 Hz, 1H), 8.38 (s, 1H), 7.83 (d, J=1.8 Hz, 1H), 7.73 (d, J=1.8 Hz, 1H), 7.41-7.30 (m, 5H), 6.45 (d, J=2.2 Hz, 1H), 4.49 (d, J=5.9 Hz, 2H); MS (m/z) 368 [M+H]+ (35Cl).

Workup

  1. customobtained in 9% yield

Sources & evidence

ORD record
ord-c6c44e4a366e4f149ffa729449386f22
Source dataset
uspto-grants-2015_05
Patent number
US09023847B2

Reaction notes

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