1-Aminocyclohexanecarboxylic acid → HCID 66720777, compound

HRID 1639909Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14](OC)=[O:15])[CH:11]=[CH:10][C:9]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:24])=[CH:4][C:3]=1[O:25][CH2:26][CH2:27][CH2:28][N:29]([CH3:31])[CH3:30].[NH2:32][C:33]1([C:39]([OH:41])=[O:40])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1>>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14]([NH:32][C:33]3([C:39]([OH:41])=[O:40])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]3)=[O:15])[CH:11]=[CH:10][C:9]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:24])=[CH:4][C:3]=1[O:25][CH2:26][CH2:27][CH2:28][N:29]([CH3:31])[CH3:30]

Participants

Reactant 2

HCID 13661-Aminocyclohexanecarboxylic acid

HCID 66720828HCID 66720828, compound

Product 1

HCID 66720777HCID 66720777, compoundYield 106.2%

Procedure

According to the saponification/peptide coupling steps described in examples 1.7 and 1.8 respectively, starting from 465 mg (1.06 mmol) of methyl 6-{4-chloro-3-[3-(dimethylamino)propoxy]phenyl}-5-(2-methylphenyl)pyridine-2-carboxylate (example 4.7) and 174 mg (1.22 mmol) of 2-aminocyclohexane-2-carboxylic acid, we obtain 330 mg of 1-({[6-{4-chloro-3-[3-(dimethylamino)propoxy]phenyl}-5-(2-methylphenyl)pyridin-2-yl]carbonyl}amino)cyclohexanecarboxylic acid hydrochloride in the form of white powder.

Sources & evidence

ORD record: ord-ff5c82a2cdab48c1a0db74c6bbb26fec
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08110579B2

Reaction notes

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