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

HRID 72535Notes

Reaction equation

HRID 72535 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:11]2[CH2:15][CH2:14][CH:13]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=3)[CH2:12]2)=[C:6]([CH:10]=1)[C:7]([OH:9])=O.Cl.[NH2:25][C:26]1([C:29]2[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][CH:30]=2)[CH2:28][CH2:27]1>>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:11]2[CH2:15][CH2:14][CH:13]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=3)[CH2:12]2)=[C:6]([CH:10]=1)[C:7]([NH:25][C:26]1([C:29]2[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][CH:30]=2)[CH2:28][CH2:27]1)=[O:9]

Participants

3

Reactant 2

HCID 66824369Methyl 4-(1-aminocyclopropyl)benzoate hydrochlorideHCID 679583935-Chloro-2-(3-(3-fluorophenoxy)pyrrolidin-1-yl)nicotinic acid

Product 1

HCID 67958327Methyl 4-(1-(5-chloro-2-(3-(3-fluorophenoxy)pyrrolidin-1-yl)nicotinamido)cyclopropyl)benzoateYield 53.8%

Procedure

The title compound (D197) (180 mg) was prepared according to the experimental procedure described in Description 146 starting from 5-chloro-2-(3-(3-fluorophenoxy)pyrrolidin-1-yl)nicotinic acid (D140) (225 mg, 0.656 mmol) and methyl 4-(1-aminocyclopropyl)benzoate (D7) (149.36 mg, 0.656 mmol).

Sources & evidence

ORD record
ord-4db401cc6fbe46aa904954edcfd084cb
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Reaction notes

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