N-(3-amino-4-methylphenyl)-3-morpholinobenzamide → N-[2-methyl-5-(3-morpholinobenzamido)phenyl]-3-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-methoxybenzamide

HRID 1369536Notes

Reaction equation

HRID 1369536 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:16]=[C:17]([CH:21]=[CH:22][C:23]=2[O:24][CH3:25])[C:18](O)=[O:19])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:26][C:27]1[CH:28]=[C:29]([NH:34][C:35](=[O:48])[C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([N:42]3[CH2:47][CH2:46][O:45][CH2:44][CH2:43]3)[CH:37]=2)[CH:30]=[CH:31][C:32]=1[CH3:33]>>[CH3:33][C:32]1[CH:31]=[CH:30][C:29]([NH:34][C:35](=[O:48])[C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([N:42]3[CH2:43][CH2:44][O:45][CH2:46][CH2:47]3)[CH:37]=2)=[CH:28][C:27]=1[NH:26][C:18](=[O:19])[C:17]1[CH:21]=[CH:22][C:23]([O:24][CH3:25])=[C:15]([O:14][CH:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH2:9][CH2:10]2)[CH:16]=1

Participants

3

Reactant 2

HCID 11301391N-(3-amino-4-methylphenyl)-3-morpholinobenzamideHCID 222911213-(1-Tert-butoxycarbonylpiperidin-4-yloxy)-4-methoxybenzoic acid

Product 1

HCID 22291016N-[2-methyl-5-(3-morpholinobenzamido)phenyl]-3-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-methoxybenzamideYield 48%

Procedure

Using an analogous procedure to that described in Example 25, 3-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-methoxybenzoic acid was reacted with N-(3-amino-4-methylphenyl)-3-morpholinobenzamide to give N-[2-methyl-5-(3-morpholinobenzamido)phenyl]-3-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-methoxybenzamide in 48% yield and that product was treated with trifluoroacetic acid. The reaction mixture was evaporated, water (40 ml) was added to the residue and the mixture was basified by the addition of 1N aqueous sodium hydroxide solution. The water was decanted and the residue was titurated under diethyl ether. The resultant solid was isolated, dissolved in water (30 ml) and basified by the addition of potassium carbonate. The precipitate was isolated and dried. There was thus obtained the title compound in 26% yield; NMR Spectrum: (DMSOd6) 1.48 (m, 2H), 1.9 (m, 2H), 2.18 (s, 3H), 3.19 (m, 4H), 3.75 (m, 4H), 3.83 (s, 3H), 4.39 (m, 1H), 7.1 (m, 2H), 7.21 (d, 1H), 7.4 (m, 3H), 7.6 (m, 3H), 7.79 (s, 1H), 9.72 (s, 1H), 10.1 (s, 1H); Mass Spectrum: M+H+ 545.

Sources & evidence

ORD record
ord-e1ceeb8e0c9940f089fb81cd067fbcc5
Source dataset
uspto-grants-2003_06
Patent number
US06579872B1

Reaction notes

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