2-Fluorobenzoyl chloride → HCID 67153864, compound

HRID 714325Notes

Reaction equation

HRID 714325 reaction equation
FC1C=CC=CC=1C(Cl)=O.[F:11][C:12]1[CH:13]=[C:14]([CH:18]=[C:19]([F:21])[CH:20]=1)[C:15](Cl)=[O:16].[NH2:22][C:23]1[CH:24]=[C:25]([CH:36]=[CH:37][N:38]=1)[C:26]([NH:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27]>>[CH2:29]([NH:28][C:26](=[O:27])[C:25]1[CH:36]=[CH:37][N:38]=[C:23]([NH:22][C:15](=[O:16])[C:14]2[CH:13]=[C:12]([F:11])[CH:20]=[C:19]([F:21])[CH:18]=2)[CH:24]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 3

HCID 98082-Fluorobenzoyl chlorideHCID 1456003,5-Difluorobenzoyl chlorideHCID 187528972-amino-N-benzylisonicotinamide

Product 1

HCID 67153864HCID 67153864, compoundYield 68%

Procedure

Following the procedure as describe in Example 6, making variations as required to replace 2-fluorobenzoyl chloride with 3,5-difluorobenzoyl chloride to react with 2-amino-N-benzylisonicotinamide, N-benzyl-2-(3,5-difluorobenzamido)isonicotinamide was obtained as a colorless solid in 68% yield: mp 185-187° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 11.16 (s, 1H), 9.35 (t, J=6.0 Hz, 1H), 8.54-8.50 (m, 2H), 7.75-7.71 (m, 2H), 7.58-7.47 (m, 2H), 7.31-7.21 (m, 5H), 4.46 (d, J=5.9 Hz, 2H); MS (ES+) m/z 368.5 (M+1).

Sources & evidence

ORD record
ord-55e6968c7bcd42968dca020e0c789c27
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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