3-Methoxyphenethylamine → HCID 67153852, compound

HRID 714308Notes

Reaction equation

HRID 714308 reaction equation
FC(F)(F)C1C=CC(CN)=CC=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH2:21][CH2:22][NH2:23])[CH:18]=[CH:19][CH:20]=1.[C:24]([NH:32][C:33]1[CH:34]=[C:35]([CH:39]=[CH:40][N:41]=1)[C:36](O)=[O:37])(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[C:24]([NH:32][C:33]1[CH:34]=[C:35]([CH:39]=[CH:40][N:41]=1)[C:36]([NH:23][CH2:22][CH2:21][C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([O:14][CH3:13])[CH:16]=1)=[O:37])(=[O:31])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 3

HCID 748663-MethoxyphenethylamineHCID 768044-(Trifluoromethyl)benzylamineHCID 643938512-Benzamidoisonicotinic acid

Product 1

HCID 67153852HCID 67153852, compoundYield 45%

Procedure

Following the procedure as described in Example 1, making variations as required to replace (4-(trifluoromethyl)phenyl)methanamine with 2-(3-methoxyphenyl)ethanamine to react with 2-benzamidoisonicotinic acid, 2-benzamido-N-[2-(3-methoxyphenyl)ethyl]isonicotinamide was obtained as a colorless solid in 45% yield: 1H NMR (300 MHz, DMSO-d6) δ 10.98 (s, 1H), 8.88 (t, J=5.5 Hz, 1H), 8.57 (s, 1H), 8.52-8.49 (m, 1H), 8.07-8.04 (m, 2H), 7.63-7.48 (m, 4H), 7.24-7.17 (m, 1H), 6.84-6.76 (m, 3H), 3.73 (s, 3H), 3.55-3.48 (m, 2H), 2.85 (t, J=7.3 Hz, 2H); MS (ES+) m/z 376.5 (M+1).

Sources & evidence

ORD record
ord-6223c07c1b2c45bdb55a25bc1688f056
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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