4-Methylbenzylamine → 2-benzamido-N-(4-methylbenzyl)-isonicotinamide

HRID 714303Notes

Reaction equation

HRID 714303 reaction equation
F[C:2](F)(F)[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH2:10])=[CH:5][CH:4]=1.CC1C=CC(CN)=CC=1.[C:22]([NH:30][C:31]1[CH:32]=[C:33]([CH:37]=[CH:38][N:39]=1)[C:34](O)=[O:35])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[C:22]([NH:30][C:31]1[CH:32]=[C:33]([CH:37]=[CH:38][N:39]=1)[C:34]([NH:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([CH3:2])=[CH:4][CH:5]=1)=[O:35])(=[O:29])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 3

HCID 660354-MethylbenzylamineHCID 768044-(Trifluoromethyl)benzylamineHCID 643938512-Benzamidoisonicotinic acid

Product 1

HCID 671538122-benzamido-N-(4-methylbenzyl)-isonicotinamideYield 35%

Procedure

Following the procedure as described in Example 1, making variations as required to replace (4-(trifluoromethyl)phenyl)methanamine with p-tolylmethanamine to react with 2-benzamidoisonicotinic acid, 2-benzamido-N-(4-methylbenzyl)-isonicotinamide was obtained as a colorless solid in 35% yield: mp 135-138° C. (dichloromethane/hexanes); 1H NMR (300 MHz, DMSO-d6) δ 11.02 (s, 1H), 9.33-9.30 (m, 1H), 8.60-8.51 (m, 2H), 8.06-8.03 (m, 2H), 7.63-7.50 (m, 4H), 6.25-7.03 (m, 4H), 4.45 (d, J=6.0 Hz, 2H), 2.28 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 166.0, 164.7, 152.8, 148.4, 143.6, 136.1, 135.9, 133.8, 131.9, 128.8, 128.3, 127.9, 127.3, 117.2, 112.7, 42.4, 20.6; MS (ES+) m/z 346.5 (M+1).

Sources & evidence

ORD record
ord-9d613baf366b4a8f95f8e0549314ea91
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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