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

HRID 72505Notes

Reaction equation

HRID 72505 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:11]2[CH2:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)([OH:15])[CH2:12]2)=[C:6]([CH:10]=1)[C:7](O)=[O:8].Cl.[NH2:24][C:25]1([C:28]2[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=2)[CH2:27][CH2:26]1>>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:11]2[CH2:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)([OH:15])[CH2:12]2)=[C:6]([CH:10]=1)[C:7]([NH:24][C:25]1([C:28]2[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=2)[CH2:27][CH2:26]1)=[O:8]

Participants

3

Reactant 2

HCID 66824369Methyl 4-(1-aminocyclopropyl)benzoate hydrochlorideHCID 679586675-Chloro-2-(3-(3-fluorophenyl)-3-hydroxyazetidin-1-yl)nicotinic acid

Product 1

HCID 67958825Methyl 4-(1-(5-chloro-2-(3-(3-fluorophenyl)-3-hydroxyazetidin-1-yl)nicotinamido)cyclopropyl)benzoateYield 66.9%

Procedure

The title compound (D161) (64.7 mg) was prepared according to the experimental procedure described in Description 146 (reaction time 1 h) starting from 5-chloro-2-(3-(3-fluorophenyl)-3-hydroxyazetidin-1-yl)nicotinic acid (D111) (63 mg, 0.195 mmol) and methyl 4-(1-aminocyclopropyl)benzoate hydrochloride (D7) (44.4 mg, 0.195 mmol).

Workup

  1. customdescribed in Description 146 (reaction time 1 h)

Sources & evidence

ORD record
ord-cbc6ca902e634c3aa41a77335b2d93f8
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Reaction notes

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