2-Amino-5-chlorobenzamide → HCID 86644192, compound

HRID 1014423Notes

Reaction equation

HRID 1014423 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]([Cl:32])=[CH:28][C:24]=1[C:25]([NH2:27])=[O:26]>>[Cl:32][C:29]1[CH:30]=[CH:31][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)=[C:24]([CH:28]=1)[C:25]([NH2:27])=[O:26]

Participants

3

Reactant 2

HCID 788762-Amino-5-chlorobenzamideHCID 534868282,4-dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 86644192HCID 86644192, compound

Procedure

Using General Protocol II and starting with 2,4-dichloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine (2.5 g, 7.3 mmol) and 2-amino-5-chlorobenzamide (3.73 g, 22 mmol), 5-chloro-2-({2-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)benzamide was isolated as a yellow solid (2.0 g, 57% Yield); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.36 (s, 3 H), 6.70 (d, J=4.03 Hz, 1 H), 7.47 (d, J=8.23 Hz, 2 H), 7.64 (dd, J=8.87, 2.47 Hz, 1 H), 7.76 (d, J=3.84 Hz, 1 H), 7.88 (d, J=2.38 Hz, 2 H), 7.98 (d, J=8.60 Hz, 2 H), 8.38 (s, 1 H), 8.41 (d, J=8.97 Hz, 1 H), 12.14 (s, 1 H).

Sources & evidence

ORD record
ord-3dadb82c8851495481e0523faaa0111a
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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