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

HRID 72514Notes

Reaction equation

HRID 72514 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:11]2[CH2:14][CH:13]([N:15]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[CH3:24])[CH3:16])[CH2:12]2)=[C:6]([CH:10]=1)[C:7](O)=[O:8].Cl.[NH2:26][C:27]1([C:30]2[CH:39]=[CH:38][C:33]([C:34]([O:36][CH3:37])=[O:35])=[CH:32][CH:31]=2)[CH2:29][CH2:28]1>>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:11]2[CH2:12][CH:13]([N:15]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[CH3:24])[CH3:16])[CH2:14]2)=[C:6]([CH:10]=1)[C:7]([NH:26][C:27]1([C:30]2[CH:39]=[CH:38][C:33]([C:34]([O:36][CH3:37])=[O:35])=[CH:32][CH:31]=2)[CH2:29][CH2:28]1)=[O:8]

Participants

3

Reactant 2

HCID 66824369Methyl 4-(1-aminocyclopropyl)benzoate hydrochlorideHCID 679582345-Chloro-2-(3-((4-fluoro-2-methylphenyl)(methyl)amino)azetidin-1-yl)nicotinic acid

Product 1

HCID 67958583Methyl 4-(1-(5-chloro-2-(3-((4-fluoro-2-methylphenyl)(methyl)amino)azetidin-1-yl)nicotinamido)cyclopropyl)benzoateYield 70.6%

Procedure

The title compound (D171) (58 mg) was prepared according to the experimental procedure described in Description 169 (reaction time 2 h) starting from 5-chloro-2-(3-((4-fluoro-2-methylphenyl)(methyl)amino)azetidin-1-yl)nicotinic acid (D120) (55 mg, 0.157 mmol) and methyl 4-(1-aminocyclopropyl)benzoate (D7) (35.8 mg, 0.157 mmol).

Workup

  1. customdescribed in Description 169 (reaction time 2 h)

Sources & evidence

ORD record
ord-4ec9055b0308403eb7b7ce2262b142e3
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Reaction notes

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