Methyl 4-(1-aminocyclopropyl)benzoate hydrochloride → Methyl 4-(1-(5-chloro-2-(3-(3,4-difluorophenoxy)azetidin-1-yl)nicotinamido)cyclopropyl)benzoate

HRID 72499

Reaction equation

HRID 72499 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:11]2[CH2:14][CH:13]([O:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[C:18]([F:23])[CH:17]=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[CH2:12][CH:13]([O:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[C:18]([F:23])[CH:17]=3)[CH2:14]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 679585205-Chloro-2-(3-(3,4-difluorophenoxy)azetidin-1-yl)nicotinic acid

Product 1

HCID 67958829Methyl 4-(1-(5-chloro-2-(3-(3,4-difluorophenoxy)azetidin-1-yl)nicotinamido)cyclopropyl)benzoateYield 38.2%

Procedure

The title compound (D155) (50 mg) was prepared according to the experimental procedure described in Description 144 starting from 5-chloro-2-(3-(3,4-difluorophenoxy)azetidin-1-yl)nicotinic acid (D109) (87 mg, 0.255 mmol) and methyl 4-(1-aminocyclopropyl)benzoate (D7) (58.14 mg, 0.255 mmol).

Sources & evidence

ORD record
ord-0fe9306e461e4e0cbd1fe167c666f0bc
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Linked notes

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