O-Methyltyramine → HCID 67153833, compound

HRID 714309Notes

Reaction equation

HRID 714309 reaction equation
FC(F)(F)C1C=CC(CN)=CC=1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][NH2:23])=[CH:17][CH:16]=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:18]1[CH:19]=[CH:20][C:15]([O:14][CH3:13])=[CH:16][CH:17]=1)=[O:37])(=[O:31])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 3

HCID 4657O-MethyltyramineHCID 768044-(Trifluoromethyl)benzylamineHCID 643938512-Benzamidoisonicotinic acid

Product 1

HCID 67153833HCID 67153833, compoundYield 48%

Procedure

Following the procedure as described in Example 1, making variations as required to replace (4-(trifluoromethyl)phenyl)methanamine with 2-(4-methoxyphenyl)ethanamine to react with 2-benzamidoisonicotinic acid, 2-benzamido-N-[2-(4-methoxyphenyl)ethyl]isonicotinamide was obtained as a colorless solid in 48% yield: 1H NMR (300 MHz, CDCl3) δ 8.79 (s, 1H), 7.91 (d, J=5.6 Hz, 2H), 7.62-7.43 (m, 4H), 7.19-7.15 (m, 4H), 6.90-6.87 (m, 2H), 6.45-6.43 (m, 1H), 3.79 (s, 3H), 3.71-3.65 (m, 2H), 2.89 (t, J=7.2 Hz, 2H); MS (ES+) m/z 376.5 (M+1).

Sources & evidence

ORD record
ord-1441f5d2245b4a0382094231a41f720e
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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