1-Aminocyclohexanecarboxylic acid → HCID 66721057, compound

HRID 1639924Notes

Reaction equation

[Cl:1][C:2]1[C:3]([C:9]2[C:10]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([O:26][CH2:27][CH2:28][CH2:29][N:30]([CH3:32])[CH3:31])[CH:20]=3)=[N:11][C:12]([C:15](OC)=[O:16])=[CH:13][CH:14]=2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[NH2:33][C:34]1([C:40]([OH:42])=[O:41])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1>>[ClH:1].[Cl:1][C:2]1[C:3]([C:9]2[C:10]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([O:26][CH2:27][CH2:28][CH2:29][N:30]([CH3:31])[CH3:32])[CH:20]=3)=[N:11][C:12]([C:15]([NH:33][C:34]3([C:40]([OH:42])=[O:41])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]3)=[O:16])=[CH:13][CH:14]=2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

Reactant 2

HCID 13661-Aminocyclohexanecarboxylic acid

HCID 66721121HCID 66721121, compound

Product 1

HCID 66721057HCID 66721057, compoundYield 96.3%

Procedure

According to the saponification/peptide coupling steps described in examples 1.7 and 1.8 respectively, starting from 1.8 g (3.62 mmol) of methyl 3,5-dichloro-2′-{4-chloro-3-[3-(dimethylamino)propoxy]phenyl}-2,3′-bipyridine-6′-carboxylate and 472 mg (3.3 mmol) of 2-aminocyclohexane-2-carboxylic acid, we obtain 1.12 g of 1-{[(3,5-dichloro-2′-{4-chloro-3-[3-(dimethylamino)propoxy]phenyl}-2,3′-bipyridin-6′-yl)carbonyl]amino}cyclohexanecarboxylic acid hydrochloride in the form of white powder.

Sources & evidence

ORD record: ord-776ae555703446d6bd417b123b063f8e
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08110579B2

Reaction notes

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