Methyl 4-(1-aminocyclopropyl)benzoate hydrochloride → Methyl 4-(1-(5-chloro-2-(3-((2-methyl-4-(trifluoromethyl)phenyl)amino)azetidin-1-yl)nicotinamido)cyclopropyl)benzoate

HRID 72513Notes

Reaction equation

HRID 72513 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:11]2[CH2:14][CH:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][C:17]=3[CH3:26])[CH2:12]2)=[C:6]([CH:10]=1)[C:7](O)=[O:8].Cl.[NH2:28][C:29]1([C:32]2[CH:41]=[CH:40][C:35]([C:36]([O:38][CH3:39])=[O:37])=[CH:34][CH:33]=2)[CH2:31][CH2:30]1>>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:11]2[CH2:12][CH:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:23])[F:24])=[CH:18][C:17]=3[CH3:26])[CH2:14]2)=[C:6]([CH:10]=1)[C:7]([NH:28][C:29]1([C:32]2[CH:41]=[CH:40][C:35]([C:36]([O:38][CH3:39])=[O:37])=[CH:34][CH:33]=2)[CH2:31][CH2:30]1)=[O:8]

Participants

3

Reactant 2

HCID 66824369Methyl 4-(1-aminocyclopropyl)benzoate hydrochlorideHCID 67958582HCID 67958582, compound

Product 1

HCID 67958042Methyl 4-(1-(5-chloro-2-(3-((2-methyl-4-(trifluoromethyl)phenyl)amino)azetidin-1-yl)nicotinamido)cyclopropyl)benzoateYield 74.7%

Procedure

The title compound (D170) (43 mg) was prepared according to the experimental procedure described in Description 169 starting from 5-chloro-2-(3-((2-methyl-4-(trifluoromethyl)phenyl)amino)azetidin-1-yl)nicotinic acid (D119) (40 mg, 0.103 mmol) and methyl 4-(1-aminocyclopropyl)benzoate (D7) (23.6 mg, 0.103 mmol).

Sources & evidence

ORD record
ord-a030f2bc9c08499287637b873bc3d3b3
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Reaction notes

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