Benzoyl chloride → 2-benzamido-N-benzyl-6-methoxyisonicotinamide

HRID 714334Notes

Reaction equation

F[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].C(Cl)(=O)C1C=CC=CC=1.[NH2:20][C:21]1[CH:22]=[C:23]([CH:34]=[C:35]([O:37][CH3:38])[N:36]=1)[C:24]([NH:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]>>[C:4]([NH:20][C:21]1[CH:22]=[C:23]([CH:34]=[C:35]([O:37][CH3:38])[N:36]=1)[C:24]([NH:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])(=[O:5])[C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:2]=1

Participants

Reactant 3

HCID 7412Benzoyl chloride

HCID 98082-Fluorobenzoyl chloride

HCID 582478622-amino-N-benzyl-6-methoxyisonicotinamide

Product 1

HCID 671538302-benzamido-N-benzyl-6-methoxyisonicotinamideYield 14%

Procedure

Following the procedure as describe in Example 6, making variations as required to replace 2-fluorobenzoyl chloride with benzoyl chloride to react with 2-amino-N-benzyl-6-methoxyisonicotinamide, 2-benzamido-N-benzyl-6-methoxyisonicotinamide was obtained as a colorless solid in 14% yield: mp 132-133° C.; 1H NMR (300 MHz, CDCl3) 8.43 (s, 1H), 8.15 (s, 1H), 7.84 (d, J=7.5 Hz, 2H), 7.57-7.43 (m, 3H), 7.34-7.23 (m, 5H), 6.98 (s, 1H), 6.87 (s, 1H), 4.57 (d, J=5.1 Hz, 2H), 3.86 (s, 3H); 13C NMR (300 MHz, CDCl3) δ 165.6, 165.3, 163.6, 149.8, 147.0, 137.6, 133.8, 132.4, 128.9, 128.7, 127.9, 127.6, 127.1, 105.2, 102.4, 54.0, 44.1; MS (ES+) m/z 362.5 (M+1).

Sources & evidence

ORD record: ord-3d4af30c632c4d729b6dcc82cff52936
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187426B2

Reaction notes

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