Trifluoroacetic acid → HCID 86644195, compound

HRID 1014426Notes

Reaction equation

HRID 1014426 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([NH2:10])=[O:9])=[C:6]([F:11])[C:5]([F:12])=[CH:4][CH:3]=1.[Cl:13][C:14]1[N:15]=[C:16](Cl)[C:17]2[CH:22]=[CH:21][N:20]([S:23]([C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[C:18]=2[N:19]=1.FC(F)(F)C(O)=O>C(O)C(F)(F)F>[Cl:13][C:14]1[N:15]=[C:16]([NH:1][C:2]2[C:7]([C:8]([NH2:10])=[O:9])=[C:6]([F:11])[C:5]([F:12])=[CH:4][CH:3]=2)[C:17]2[CH:22]=[CH:21][N:20]([S:23]([C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)(=[O:24])=[O:25])[C:18]=2[N:19]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 534868282,4-dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidineHCID 59442088HCID 59442088, compound

Product 1

HCID 86644195HCID 86644195, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 64092,2,2-TrifluoroethanolSolvent

Procedure

To a pressure flask is added 6-amino-2,3-difluorobenzamide (0.700 g, 4.07 mmol), 2,4-dichloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine (1.4 g, 4.07 mmol), trifluoroethanol (30 mL) and trifluoracetic acid (1.6 mL, 20.4 mmol). The resulting clear solution was stirred overnight. The next morning all precipitates were collected to afford analytically pure 6-({2-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-2,3-difluorobenzamide as a white solid (1.07 g, 55% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.36 (s, 3 H), 6.74 (s, 1 H), 7.41-7.48 (m, 3 H), 7.49-7.60 (m, 1 H), 7.64 (d, J=3.67 Hz, 1 H), 7.82 (s, 1 H), 7.96 (d, J=8.43 Hz, 3 H), 10.13 (s, 1 H).

Workup

  1. customThe next morning all precipitates were collected

Sources & evidence

ORD record
ord-91b6b857c9844d93b706f79242d8259c
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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