2-Fluorobenzoyl chloride → HCID 67153820, compound

HRID 714323Notes

Reaction equation

FC1C=CC=CC=1C(Cl)=O.[CH3:11][O:12][C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=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:18]=[CH:19][CH:20]=[CH:21][C:13]=2[O:12][CH3:11])[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 889692-Methoxybenzoyl chloride

HCID 187528972-amino-N-benzylisonicotinamide

Product 1

HCID 67153820HCID 67153820, compoundYield 76%

Procedure

Following the procedure as describe in Example 6, making variations as required to replace 2-fluorobenzoyl chloride with 2-methoxybenzoyl chloride to react with 2-amino-N-benzylisonicotinamide, N-benzyl-2-(2-methoxybenzamido)isonicotinamide was obtained as a colorless solid in 76% yield: mp 205-207° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 10.56 (s, 1H), 8.70 (s, 1H), 8.42 (d, J=5.1 Hz, 1H), 8.20 (dd, J=7.8, 1.8 Hz, 1H), 7.58-7.49 (m, 2H), 7.37-7.25 (m, 5H), 7.14-7.02 (m, 2H), 6.81 (s, 1H), 4.64 (d, J=5.8 Hz, 2H), 4.08 (s, 3H); MS (ES+) m/z 362.5 (M+1).

Sources & evidence

ORD record: ord-98885aae1e1e485793f14069ec406675
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187426B2

Reaction notes

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