Water → HCID 86697835, compound

HRID 2279900Notes

Reaction equation

HRID 2279900 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([NH:13][CH3:14])=[O:12])[C:5]([C:19]([F:22])([F:21])[F:20])=[CH:4][N:3]=1.[Br:23]N1C(=O)CCC1=O.O>CN(C=O)C>[Br:23][C:16]1[CH:17]=[CH:18][C:9]([NH:8][C:6]2[C:5]([C:19]([F:22])([F:20])[F:21])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=2)=[C:10]([CH:15]=1)[C:11]([NH:13][CH3:14])=[O:12]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 866338612-((2-Chloro-5-(trifluoromethyl)pyrimidin-4-yl)amino)-N-methylbenzamide

Product 1

HCID 86697835HCID 86697835, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-{[2-chloro-5-(trifluoromethyl)pyrimidin-4-yl]amino}-N-methylbenzamide (WO 2010141406, 4.6 g, 13.9 mmol) and N-bromosuccinimide (2.46 g, 13.9 mmol) were taken up in DMF (8 mL) and stirred for 1 hr. The reaction mixture was poured into water and the resulting precipitate was collected via filtration, air dried and purified by column chromatography (SiO2, 1% methanol in dichloromethane) to give 2.4 g (42%) of the title compound. 1H NMR (600 MHz, DMSO-d6) δ: 11.88 (s, 1H), 8.93 (brs, 1H), 8.67 (s, 1H), 8.28 (d, J=9 Hz, 1H), 7.95 (s, 1H), 7.76 (d, J=9 Hz, 1H), 2.75 (d, J=4.2 Hz, 3H).

Workup

  1. filtrationthe resulting precipitate was collected via filtration, air
  2. customdried
  3. custompurified by column chromatography (SiO2, 1% methanol in dichloromethane)

Sources & evidence

ORD record
ord-58a07fc44dc84d88b1a556b41f1e12a6
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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