Methyl 4-(1-aminocyclopropyl)benzoate hydrochloride → Methyl 4-(1-(2-(3-(4-fluoro-3-(trifluoromethyl)phenoxy)azetidin-1-yl)-5-(trifluoromethyl)nicotinamido)cyclopropyl)benzoate

HRID 72518

Reaction equation

HRID 72518 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:5]([O:6][CH:7]2[CH2:10][N:9]([C:11]3[N:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:12]=3[C:13](O)=[O:14])[CH2:8]2)=[CH:4][C:3]=1[C:26]([F:29])([F:28])[F:27].Cl.[NH2:31][C:32]1([C:35]2[CH:44]=[CH:43][C:38]([C:39]([O:41][CH3:42])=[O:40])=[CH:37][CH:36]=2)[CH2:34][CH2:33]1>>[F:1][C:2]1[CH:25]=[CH:24][C:5]([O:6][CH:7]2[CH2:10][N:9]([C:11]3[N:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:12]=3[C:13]([NH:31][C:32]3([C:35]4[CH:44]=[CH:43][C:38]([C:39]([O:41][CH3:42])=[O:40])=[CH:37][CH:36]=4)[CH2:34][CH2:33]3)=[O:14])[CH2:8]2)=[CH:4][C:3]=1[C:26]([F:28])([F:27])[F:29]

Participants

3

Reactant 2

HCID 66824369Methyl 4-(1-aminocyclopropyl)benzoate hydrochlorideHCID 866978752-(3-(4-Fluoro-3-(trifluoromethyl)phenoxy)azetidin-1-yl)-5-(trifluoromethyl)nicotinic acid

Product 1

HCID 86697879Methyl 4-(1-(2-(3-(4-fluoro-3-(trifluoromethyl)phenoxy)azetidin-1-yl)-5-(trifluoromethyl)nicotinamido)cyclopropyl)benzoateYield 34.3%

Procedure

The title compound (D176) (52 mg) was prepared according to the experimental procedure described in Description 144 starting from 2-(3-(4-fluoro-3-(trifluoromethyl)phenoxy)azetidin-1-yl)-5-(trifluoromethyl)nicotinic acid (D125) (108 mg, 0.254 mmol) and methyl 4-(1-aminocyclopropyl)benzoate (D7) (57.95 mg, 0.254 mmol).

Sources & evidence

ORD record
ord-77534bf9cad0429eb72b5664eb5559b5
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Linked notes

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