2-Fluorobenzoyl chloride → HCID 67153873, compound

HRID 714327Notes

Reaction equation

FC1C=CC=CC=1C(Cl)=O.[C:11]([C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1)#[N:12].[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:17](=[O:18])[C:16]2[CH:20]=[CH:21][C:13]([C:11]#[N:12])=[CH:14][CH:15]=2)[CH:24]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

Reactant 3

HCID 98082-Fluorobenzoyl chloride

HCID 801724-Cyanobenzoyl chloride

HCID 187528972-amino-N-benzylisonicotinamide

Product 1

HCID 67153873HCID 67153873, compoundYield 35%

Procedure

Following the procedure as describe in Example 6, making variations as required to replace 2-fluorobenzoyl chloride with 4-cyanobenzoyl chloride to react with 2-amino-N-benzylisonicotinamide, N-benzyl-2-(4-cyanobenzamido)isonicotinamide was obtained as a colorless solid in 35% yield: mp 180-181° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 8.97 (s, 1H), 8.63 (s, 1H), 8.41 (t, J=5.0 Hz, 1H), 8.03-8.00 (m, 2H), 7.82-7.79 (m, 2H), 7.60 (dd, J=5.1, 1.2 Hz, 1H), 7.36-7.29 (m, 5H), 6.69 (m, 1H), 4.65 (d, J=5.7 Hz, 2H); MS (ES+) m/z 357.5 (M+1).

Sources & evidence

ORD record: ord-501183eb832f433e8e22d14c552d30f8
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187426B2

Reaction notes

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