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

HRID 72517Notes

Reaction equation

HRID 72517 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[O:5][CH:6]1[CH2:9][N:8]([C:10]2[N:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:11]=2[C:12]([OH:14])=O)[CH2:7]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>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[O:5][CH:6]1[CH2:7][N:8]([C:10]2[N:18]=[CH:17][C:16]([C:19]([F:21])([F:22])[F:20])=[CH:15][C:11]=2[C:12]([NH:27][C:28]2([C:31]3[CH:40]=[CH:39][C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:33][CH:32]=3)[CH2:30][CH2:29]2)=[O:14])[CH2:9]1

Participants

3

Reactant 2

HCID 66824369Methyl 4-(1-aminocyclopropyl)benzoate hydrochlorideHCID 679583172-(3-(3-Chlorophenoxy)azetidin-1-yl)-5-(trifluoromethyl)nicotinic acid

Product 1

HCID 67958389Methyl 4-(1-(2-(3-(3-chlorophenoxy)azetidin-1-yl)-5-(trifluoromethyl)nicotinamido)cyclopropyl)benzoateYield 11.2%

Procedure

The title compound (D175) (14 mg) was prepared according to the experimental procedure described in Description 144 starting from 2-(3-(3-chlorophenoxy)azetidin-1-yl)-5-(trifluoromethyl)nicotinic acid (D124) (85 mg, 0.228 mmol) and methyl 4-(1-aminocyclopropyl)benzoate (D7) (51.92 mg, 0.228 mmol).

Sources & evidence

ORD record
ord-59f9eb84b33e4e7bbf30746e0729fbfe
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Reaction notes

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