4-(Trifluoromethyl)benzylamine → 2-benzamido-N-[2-(2-chlorophenyl)ethyl]-isonicotinamide

HRID 714304Notes

Reaction equation

HRID 714304 reaction equation
FC(F)(F)C1C=CC(CN)=CC=1.[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][CH2:21][NH2:22].[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][CH2:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[Cl:13])=[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 831172-(2-Chlorophenyl)ethylamineHCID 643938512-Benzamidoisonicotinic acid

Product 1

HCID 671538542-benzamido-N-[2-(2-chlorophenyl)ethyl]-isonicotinamideYield 27%

Procedure

Following the procedure as described in Example 1, making variations as required to replace (4-(trifluoromethyl)phenyl)methanamine with 2-(2-chlorophenyl)ethanamine to react with 2-benzamidoisonicotinic acid, 2-benzamido-N-[2-(2-chlorophenyl)ethyl]-isonicotinamide was obtained as a colorless solid in 27% yield: 1H NMR (300 MHz, DMSO-d6) δ 10.91-10.82 (m, 1H), 8.91-8.85 (m, 1H), 8.56-8.44 (m, 2H), 8.06-7.98 (m, 2H), 7.63-7.17 (m, 8H), 3.55-3.48 (m, 2H), 3.03-2.92 (m, 2H); MS (ES+) m/z 380.5 (M+1), 382.3 (M+2).

Sources & evidence

ORD record
ord-12a11ed153234fb299ea4dfa7f02206f
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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