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

HRID 1014417Notes

Reaction equation

HRID 1014417 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]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][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]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][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 140230022-Amino-4-methoxybenzamideHCID 534868282,4-dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 866441862-({2-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-4-(methyloxy)benzamideYield 29%

Procedure

Using General Protocol II and starting with 2,4-dichloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine (4.0 g, 11.7 mmol) and 2-amino-4-(methyloxy)benzamide (4.5 g, 26.8 mmol), 2-({2-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-4-(methyloxy)benzamide was isolated as a yellow solid (0.1.58 g, 29% yield); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.33 (s, 3 H), 4.28 (s, 3 H), 6.62 (t, J=3.48 Hz, 1 H), 6.68 (ddd, J=6.00, 2.88, 2.66 Hz, 1 H), 7.41-7.46 (m, 2 H), 7.64 (s, 1 H), 7.74 (t, J=3.48 Hz, 1 H), 7.81-7.87 (m, 1 H), 7.92-7.98 (m, 2 H), 8.22 (s, 1 H), 8.32 (t, J=2.66 Hz, 1 H), 13.13 (s, 1 H).

Sources & evidence

ORD record
ord-0d10695b5d0d48f1b2b65e7d5535e42a
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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