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

HRID 1369540Notes

Reaction equation

HRID 1369540 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=2)[C:17]([OH:19])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:23][C:24]1[CH:25]=[C:26]([NH:31][C:32](=[O:45])[C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([N:39]3[CH2:44][CH2:43][O:42][CH2:41][CH2:40]3)[CH:34]=2)[CH:27]=[CH:28][C:29]=1[CH3:30]>>[CH3:30][C:29]1[CH:28]=[CH:27][C:26]([NH:31][C:32](=[O:45])[C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([N:39]3[CH2:40][CH2:41][O:42][CH2:43][CH2:44]3)[CH:34]=2)=[CH:25][C:24]=1[NH:23][C:17](=[O:19])[C:16]1[CH:20]=[CH:21][CH:22]=[C:14]([O:13][CH:10]2[CH2:11][CH2:12][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9]2)[CH:15]=1

Participants

3

Reactant 2

HCID 11301391N-(3-amino-4-methylphenyl)-3-morpholinobenzamideHCID 222911363-{[1-(tert-Butoxycarbonyl)pyrrolidin-3-yl]oxy}benzoic acid

Product 1

HCID 22291045N-[2-methyl-5-(3-morpholinobenzamido)phenyl]-3-(1-tert-butoxycarbonylpyrrolidin-3-yloxy)benzamideYield 58%

Procedure

Using an analogous procedure to that described in the first paragraph of Example 25, 3-(1-tert-butoxycarbonylpyrrolidin-3-yloxy)benzoic acid was reacted with N-(3-amino-4-methylphenyl)-3-morpholinobenzamide to give N-[2-methyl-5-(3-morpholinobenzamido)phenyl]-3-(1-tert-butoxycarbonylpyrrolidin-3-yloxy)benzamide in 58% yield; NMR Spectrum: (DMSOd6) 1.38 (s, 9H), 2.1 (m, 2H), 2.18 (s, 3H), 3.18 (t, 4H), 3.35 (m, 1H), 3.41 (m, 2H), 3.75 (t, 4H), 5.1 (m, 1H), 7.12 (td, 1H), 7.21 (d, 1H), 7.37 (m, 3H), 7.41 (t, 2H), 7.5 (s, 1H), 7.57 (d, 1H), 7.78 (d, 1H), 9.83 (s, 1H), 10.1 (s, 1H); Mass Spectrum: M+H+ 601.

Sources & evidence

ORD record
ord-70274385d5f14d9b9080adb4ae693ca9
Source dataset
uspto-grants-2003_06
Patent number
US06579872B1

Reaction notes

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