4-(Trifluoromethyl)benzylamine → 2-benzamido-N-(3,5-dichlorobenzyl)isonicotinamide

HRID 714302Notes

Reaction equation

HRID 714302 reaction equation
FC(F)(F)C1C=CC(CN)=CC=1.[Cl:13][C:14]1[CH:15]=[C:16]([CH2:21][NH2:22])[CH:17]=[C:18]([Cl:20])[CH:19]=1.[C:23]([NH:31][C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][N:40]=1)[C:35](O)=[O:36])(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[C:23]([NH:31][C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][N:40]=1)[C:35]([NH:22][CH2:21][C:16]1[CH:15]=[C:14]([Cl:13])[CH:19]=[C:18]([Cl:20])[CH:17]=1)=[O:36])(=[O:30])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 3

HCID 768044-(Trifluoromethyl)benzylamineHCID 457602Benzenemethanamine, 3,5-dichloro-HCID 643938512-Benzamidoisonicotinic acid

Product 1

HCID 671537982-benzamido-N-(3,5-dichlorobenzyl)isonicotinamideYield 41%

Procedure

Following the procedure as described in Example 1, making variations as required to replace (4-(trifluoromethyl)phenyl)methanamine with (3,5-dichlorophenyl)-methanamine to react with 2-benzamidoisonicotinic acid, 2-benzamido-N-(3,5-dichlorobenzyl)isonicotinamide was obtained as a colorless solid in 41% yield: mp 248-251° C. (dichloromethane/hexanes); 1H NMR (300 MHz, DMSO-d6) δ 11.01 (br s, 1H), 9.42 (br s, 1H), 8.63-8.54 (m, 2H), 8.06 (s, 2H), 7.60-7.39 (m, 7H), 4.53-4.51 (d, J=4.5 Hz, 2H).

Sources & evidence

ORD record
ord-93db325307b245aeb89d06ed8a0419c7
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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