2-Amino-6-methoxybenzamide → 2-({2-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-6-(methyloxy)benzamide

HRID 1014415Notes

Reaction equation

HRID 1014415 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:6]=2[N:7]=1.[NH2:22][C:23]1[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH3:33])[C:24]=1[C:25]([NH2:27])=[O:26]>>[Cl:1][C:2]1[N:3]=[C:4]([NH:22][C:23]2[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH3:33])[C:24]=2[C:25]([NH2:27])=[O:26])[C:5]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:6]=2[N:7]=1

Participants

3

Reactant 2

HCID 122648142-Amino-6-methoxybenzamideHCID 534868282,4-dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 866441842-({2-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-6-(methyloxy)benzamide

Procedure

Using General Protocol II with 2,4-dichloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine (3.00 g, 8.8 mmol) and 2-amino-6-(methyloxy)benzamide (3.10 g, 18.7 mmol), 2-({2-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-6-(methyloxy)benzamide was isolated as white solid (1.15 g, 28% Yield); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.34 (s, 3 H), 3.81 (s, 3 H), 6.55 (s, 1 H), 6.94 (d, J=7.87 Hz, 1 H), 7.37-7.49 (m, 4 H), 7.63 (d, J=4.03 Hz, 3 H), 7.94 (d, J=8.24 Hz, 2 H), 10.98 (s, 1 H).

Sources & evidence

ORD record
ord-37ffdca16f2644209e9acc053fde8d5a
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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