2-Amino-5-methoxybenzamide → HCID 86644185, compound

HRID 1014416Notes

Reaction equation

HRID 1014416 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][C:29]([O:32][CH3:33])=[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]=[CH:30][C:29]([O:32][CH3:33])=[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 203382172-Amino-5-methoxybenzamideHCID 534868282,4-dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 86644185HCID 86644185, compound

Procedure

Using General Protocol II and starting with 2,4-dichloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine (1.64 g, 4.82 mmol) and 2-amino-5-(methyloxy)benzamide (1.0 g, 6.00 mmol), 2-({2-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-5-(methyloxy)benzamide was isolated as a white solid (1.83 g, 81% Yield); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.36 (s, 3 H), 3.79 (s, 3 H), 6.61 (s, 1 H), 7.15 (dd, J=8.97, 2.93 Hz, 1 H), 7.31 (d, J=2.93 Hz, 1 H), 7.46 (d, J=8.05 Hz, 2 H), 7.67 (d, J=4.03 Hz, 2 H), 7.96 (ddd, J=8.60, 2.01, 1.83 Hz, 2 H), 8.08 (d, J=8.78 Hz, 1 H), 8.15 (s, 1 H), 11.48 (s, 1 H).

Sources & evidence

ORD record
ord-dc858e90e19a47458516514a3575ed67
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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