2-Fluorobenzoyl chloride → HCID 67153850, compound

HRID 714332Notes

Reaction equation

HRID 714332 reaction equation
FC1C=CC=CC=1C(Cl)=O.[F:11][C:12]([F:23])([F:22])[C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16](Cl)=[O:17].[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:16](=[O:17])[C:15]2[CH:19]=[CH:20][CH:21]=[C:13]([C:12]([F:23])([F:22])[F:11])[CH:14]=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 752573-(Trifluoromethyl)benzoyl chlorideHCID 187528972-amino-N-benzylisonicotinamide

Product 1

HCID 67153850HCID 67153850, compoundYield 80%

Procedure

Following the procedure as describe in Example 6, making non-critical variations as required to replace 2-fluorobenzoyl chloride with 3-(trifluoromethyl)benzoyl chloride to react with 2-amino-N-benzylisonicotinamide, N-benzyl-2-(3-(trifluoromethyl)benzamido)-isonicotinamide was obtained as a colorless solid in 80% yield: mp 126-128° C.; 1H NMR (300 MHz, CDCl3) δ 10.36 (s, 1H), 8.82 (s, 1H), 8.41-8.14 (m, 4H), 7.95-7.27 (m, 7H), 7.03 (s, 1H), 4.57 (d, J=5.1 Hz, 2H); MS (ES+) m/z 400.5 (M+1).

Sources & evidence

ORD record
ord-7b8475104b3c4cf8842381806bd70b0f
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

Loading…