2-Fluorobenzoyl chloride → HCID 67153790, compound

HRID 714328Notes

Reaction equation

HRID 714328 reaction equation
FC1C=CC=CC=1C(Cl)=O.[CH3:11][N:12]([CH3:22])[C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1.[NH2:23][C:24]1[CH:25]=[C:26]([CH:37]=[CH:38][N:39]=1)[C:27]([NH:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28]>>[CH2:30]([NH:29][C:27](=[O:28])[C:26]1[CH:37]=[CH:38][N:39]=[C:24]([NH:23][C:17](=[O:18])[C:16]2[CH:20]=[CH:21][C:13]([N:12]([CH3:22])[CH3:11])=[CH:14][CH:15]=2)[CH:25]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

4

Reactant 3

HCID 98082-Fluorobenzoyl chlorideHCID 44007824-(Dimethylamino)benzoyl chlorideHCID 187528972-amino-N-benzylisonicotinamide

Product 1

HCID 67153790HCID 67153790, compoundYield 7%

Procedure

Following the procedure as describe in Example 6, making variations as required to replace 2-fluorobenzoyl chloride with 4-(dimethylamino)benzoyl chloride to react with 2-amino-N-benzylisonicotinamide, N-benzyl-2-(4-(dimethylamino)benzamido)-isonicotinamide was obtained as a colorless solid in 7% yield: mp 160-165° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, DMSO-d6) δ 10.49 (s, 1H), 9.28 (t, J=5.9 Hz, 1H), 8.54 (s, 1H), 8.44 (d, J=5.1 Hz, 1H), 7.93 (d, J=9.0 Hz, 2H), 7.46 (dd, J=5.1, 1.4 Hz, 1H), 7.36-7.16 (m, 5H), 6.70 (d, J=9.1 Hz, 2H), 4.43 (d, J=5.9 Hz, 2H), 2.96 (s, 6H); MS (ES+) m/z 375.5 (M+1).

Sources & evidence

ORD record
ord-9049479ecc49425795da0231b37de450
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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