2-Fluorobenzoyl chloride → HCID 21905816, compound

HRID 1246786Notes

Reaction equation

HRID 1246786 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[Cl:11][C:12]1[N:17]=[C:16]([CH3:18])[N:15]=[C:14]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[C:13]=1[NH2:27]>N1C=CC=CC=1>[Cl:11][C:12]1[C:13]([NH:27][C:4](=[O:5])[C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=2[F:1])=[C:14]([NH:19][C:20]2[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=2)[N:15]=[C:16]([CH3:18])[N:17]=1

Participants

4

Reactant 2

HCID 98082-Fluorobenzoyl chloride2×HCID 21905766HCID 21905766, compound

Product 1

HCID 21905816HCID 21905816, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Fluorobenzoyl chloride (93 μl, 0.78 mmol) was added to 6-chloro-N4-(4-chlorophenyl)-2-methylpyrimidine-4,5-diamine I-(7A-80)a (173 mg) and pyridine (1 ml) and stirred at room temperature for 7 h. The reaction was incomplete at this time so an additional 1.5 equivalents of 2-fluorobenzoyl chloride was added to the reaction mixture and continued stirring overnight at room temperature. The reaction was extracted from saturated NaHCO3 solution into ethyl acetate. The organic layers were combined, dried (Na2SO4), filtered, and concentrated to dryness to afford the desired crude product I-(7A-80)b (0.25 g): +ESI MS (M+1) 391.2.

Workup

  1. additionwas added to the reaction mixture
  2. stirringcontinued stirring overnight at room temperature
  3. extractionThe reaction was extracted from saturated NaHCO3 solution into ethyl acetate
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-2375f8f8064a4d01bb1f4e35b218b86b
Source dataset
uspto-grants-2006_10
Patent number
US07129239B2

Reaction notes

Loading…