p-Anisoyl chloride → HCID 67153846, compound

HRID 714322Notes

Reaction equation

FC1C=CC=CC=1C(Cl)=O.[CH3:11][O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1.[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]([O:12][CH3:11])=[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 7477p-Anisoyl chloride

HCID 98082-Fluorobenzoyl chloride

HCID 187528972-amino-N-benzylisonicotinamide

Product 1

HCID 67153846HCID 67153846, compoundYield 28%

Procedure

Following the procedure as describe in Example 6, making variations as required to replace 2-fluorobenzoyl chloride with 4-methoxybenzoyl chloride to react with 2-amino-N-benzylisonicotinamide, N-benzyl-2-(4-methoxybenzamido)isonicotinamide was obtained as a colorless solid in 28% yield: mp 165-166° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 8.91 (s, 1H), 8.65 (s, 1H), 8.38 (d, J=5.2 Hz, 1H), 7.91-7.86 (m, 2H), 7.58 (dd, J=5.2, 1.5 Hz, 1H), 7.34-7.25 (m, 5H), 6.99-6.94 (m, 2H), 6.77 (s, 1H), 4.64 (d, J=5.8 Hz, 2H), 3.86 (s, 3H); MS (ES+) m/z 362.5 (M+1).

Sources & evidence

ORD record: ord-89e60cdb603549aa8bd7c9c5a4dc2457
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187426B2

Reaction notes

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