Methyl 4-(1-aminocyclopropyl)benzoate hydrochloride → HCID 67958452, compound

HRID 72536Notes

Reaction equation

HRID 72536 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:18]=[C:19]([CH3:23])[CH:20]=[CH:21][CH:22]=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:18]=[C:19]([CH3:23])[CH:20]=[CH:21][CH:22]=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 67958386HCID 67958386, compound

Product 1

HCID 67958452HCID 67958452, compoundYield 5%

Procedure

The title compound (D198) (12 mg) was prepared according to the experimental procedure described in Description 146 starting from 5-chloro-2-(3-(m-tolyloxy)pyrrolidin-1-yl)nicotinic acid (D141) (160 mg, 0.472 mmol) and methyl 4-(1-aminocyclopropyl)benzoate (D7) (107.46 mg, 0.472 mmol). The residue (50 mg) obtained from SPE-Si cartridge purification (50 mg) dissolved in a mixture of chloroform/ethanol (1/1) (1 ml) was separated by chiral HPLC [Phenomenex Lux1 column (250×20 mm, 5 μm particle size). Mobile phase: isocratic premixed mixture of (hexane 80%, ethanol 20%) containing 0.1% of diethylamine. Flow rate=10 ml/min. UV detection: 245 nm]. Collected fractions, after solvent evaporation, afforded the title compound (D198) (12 mg)

Sources & evidence

ORD record
ord-37303e6f6f2448eaaebb5429e9b1089f
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Reaction notes

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