2-Fluorobenzoyl chloride → HCID 67153850, compound

HRID 714333Notes

Reaction equation

HRID 714333 reaction equation
F[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[F:11][C:12]([F:23])([F:22])C1C=CC=CC=1C(Cl)=O.[NH2:24][C:25]1[CH:26]=[C:27]([CH:38]=[CH:39][N:40]=1)[C:28]([NH:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29]>>[CH2:31]([NH:30][C:28](=[O:29])[C:27]1[CH:38]=[CH:39][N:40]=[C:25]([NH:24][C:4](=[O:5])[C:3]2[CH:7]=[CH:8][CH:9]=[C:10]([C:12]([F:23])([F:22])[F:11])[CH:2]=2)[CH:26]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 3

HCID 98082-Fluorobenzoyl chlorideHCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 187528972-amino-N-benzylisonicotinamide

Product 1

HCID 67153850HCID 67153850, compoundYield 73%

Procedure

Following the procedure as describe in Example 6, making variations as required to replace 2-fluorobenzoyl chloride with 2-(trifluoromethyl)benzoyl chloride to react with 2-amino-N-benzylisonicotinamide, N-benzyl-2-(3-(trifluoromethyl)benzamido)-isonicotinamide was obtained as a colorless solid in 73% yield: mp 87-88° C.; 1H NMR (300 MHz, CDCl3) δ 10.09 (s, 1H), 8.58 (s, 1H), 7.82-6.95 (m, 12H), 4.57 (d, J=5.1 Hz, 2H); MS (ES+) m/z 400.5 (M+1).

Sources & evidence

ORD record
ord-b0dca14ff87f45c5bf36459f059f0e57
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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