2-Fluorobenzoyl chloride → HCID 67153799, compound

HRID 714321Notes

Reaction equation

HRID 714321 reaction equation
FC1C=CC=CC=1C(Cl)=O.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16](Cl)=[O:17].[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:16](=[O:17])[C:15]2[CH:19]=[CH:20][CH:21]=[C:13]([O:12][CH3:11])[CH:14]=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 74374m-Anisoyl chlorideHCID 187528972-amino-N-benzylisonicotinamide

Product 1

HCID 67153799HCID 67153799, compoundYield 46%

Procedure

Following the procedure as describe in Example 6, making variations as required to replace 2-fluorobenzoyl chloride with 3-methoxybenzoyl chloride to react with 2-amino-N-benzylisonicotinamide, N-benzyl-2-(3-methoxybenzamido)isonicotinamide was obtained as a colorless solid in 46% yield: mp 95-96° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 8.88 (s, 1H), 8.64 (s, 1H), 8.36 (d, J=5.1 Hz, 1H), 7.56 (dd, J=5.1, 1.4 Hz, 1H), 7.43-7.25 (m, 8H), 7.11-7.07 (m, 1H), 6.80 (t, J=4.7 Hz, 1H), 4.63 (d, J=5.8 Hz, 2H), 3.84 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 165.8, 165.1, 160.0, 151.9, 148.6, 144.2, 137.4, 135.0, 129.9, 128.8, 128.0, 127.8, 118.9, 118.8, 118.6, 112.4, 110.5, 55.5, 44.2; MS (ES+) m/z 362.5 (M+1).

Sources & evidence

ORD record
ord-8316362539b849b6bb81b8ce06d0b046
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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