2-Amino-5-fluorobenzamide → 2-({2-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-5-fluorobenzamide

HRID 1014420Notes

Reaction equation

HRID 1014420 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]([F:32])=[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]([F:32])=[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 102410032-Amino-5-fluorobenzamideHCID 534868282,4-dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 866441892-({2-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-5-fluorobenzamide

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-5-fluorobenzamide (4.0 g, 26 mmol), 2-({2-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-5-fluorobenzamide was isolated as a white solid (3.05 g, 76% Yield); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.36 (s, 3 H), 6.68 (d, J=4.03 Hz, 1 H), 7.42-7.50 (m, 3 H), 7.65 (dd, J=9.51, 3.11 Hz, 1 H), 7.72 (d, J=3.84 Hz, 1 H), 7.83 (s, 1 H), 7.97 (dt, J=8.65, 1.90 Hz, 2 H), 8.26 (s, 1 H), 8.30 (dd, J=9.15, 5.12 Hz, 1 H), 11.81 (s, 1 H).

Sources & evidence

ORD record
ord-39bf33da28d143fc907854708d861ade
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

Loading…