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

HRID 72516Notes

Reaction equation

HRID 72516 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]([OH:15])=O)[CH2:8]2)=[CH:4][CH:3]=1.Cl.[NH2:27][C:28]1([C:31]2[CH:40]=[CH:39][C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:33][CH:32]=2)[CH2:30][CH2:29]1>>[F:1][C:2]1[CH:25]=[CH:24][C:5]([O:6][CH:7]2[CH2:8][N:9]([C:11]3[N:19]=[CH:18][C:17]([C:20]([F:22])([F:21])[F:23])=[CH:16][C:12]=3[C:13]([NH:27][C:28]3([C:31]4[CH:40]=[CH:39][C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:33][CH:32]=4)[CH2:30][CH2:29]3)=[O:15])[CH2:10]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 66824369Methyl 4-(1-aminocyclopropyl)benzoate hydrochlorideHCID 679583872-(3-(4-Fluorophenoxy)azetidin-1-yl)-5-(trifluoromethyl)nicotinic acid

Product 1

HCID 67958364Methyl 4-(1-(2-(3-(4-fluorophenoxy)azetidin-1-yl)-5-(trifluoromethyl)nicotinamido)cyclopropyl)benzoateYield 60%

Procedure

The title compound (D173) (80 mg) was prepared according to the experimental procedure described in Description 146 starting from 2-(3-(4-fluorophenoxy)azetidin-1-yl)-5-(trifluoromethyl)nicotinic acid (D122) (90 mg, 0.252 mmol) and methyl 4-(1-aminocyclopropyl)benzoate (D7) (57.51 mg, 0.252 mmol).

Sources & evidence

ORD record
ord-7479a85bb0ca473393893f9cb9508824
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Reaction notes

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