2-Amino-4-chlorobenzamide → HCID 86644193, compound

HRID 1014424Notes

Reaction equation

HRID 1014424 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]([Cl:32])[CH:29]=[CH:28][C:24]=1[C:25]([NH2:27])=[O:26]>>[Cl:32][C:30]1[CH:29]=[CH:28][C:24]([C:25]([NH2:27])=[O:26])=[C:23]([NH:22][C:4]2[C:5]3[CH:10]=[CH:9][N:8]([S:11]([C:14]4[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=4)(=[O:13])=[O:12])[C:6]=3[N:7]=[C:2]([Cl:1])[N:3]=2)[CH:31]=1

Participants

3

Reactant 2

HCID 123748372-Amino-4-chlorobenzamideHCID 534868282,4-dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 86644193HCID 86644193, compound

Procedure

Using General Protocol II and starting with 2,4-dichloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine (3.0 g, 8.8 mmol) and 2-amino-4-chlorobenzamide (3.0 g, 17.6 mmol), 4-chloro-2-({2-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)benzamide was isolated as a yellow solid (0.650 g, 16% Yield); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.36 (s, 3 H), 6.68 (d, J=4.03 Hz, 1 H), 7.23 (dd, J=8.51, 2.10 Hz, 1 H), 7.47 (d, J=8.23 Hz, 2 H), 7.79 (d, J=4.03 Hz, 1 H), 7.87 (d, J=8.42 Hz, 1 H), 7.91 (s, 1 H), 7.98 (d, J=8.42 Hz, 2 H), 8.41 (s, 1 H), 8.66 (d, J=2.20 Hz, 1 H), 12.65 (s, 1 H).

Sources & evidence

ORD record
ord-b76010ee8b6c4ca4b32b946e253d3643
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

Loading…