9-aminobicyclo[3.3.1]nonane-9-carboxylic Acid → 9-({[6-{4-Chloro-3-[3-(dimethylamino)propoxy]phenyl}-5-(2,6-dimethoxyphenyl)pyridin-2-yl]carbonyl}amino)bicyclo[3.3.1]nonane-9-carboxylic acid hydrochloride

HRID 1040338Notes

Reaction equation

HRID 1040338 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14](O)=[O:15])[CH:11]=[CH:10][C:9]=2[C:17]2[C:22]([O:23][CH3:24])=[CH:21][CH:20]=[CH:19][C:18]=2[O:25][CH3:26])=[CH:4][C:3]=1[O:27][CH2:28][CH2:29][CH2:30][N:31]([CH3:33])[CH3:32].[NH2:34][C:35]1([C:44]([OH:46])=[O:45])[CH:40]2[CH2:41][CH2:42][CH2:43][CH:36]1[CH2:37][CH2:38][CH2:39]2>>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14]([NH:34][C:35]3([C:44]([OH:46])=[O:45])[CH:40]4[CH2:41][CH2:42][CH2:43][CH:36]3[CH2:37][CH2:38][CH2:39]4)=[O:15])[CH:11]=[CH:10][C:9]=2[C:17]2[C:22]([O:23][CH3:24])=[CH:21][CH:20]=[CH:19][C:18]=2[O:25][CH3:26])=[CH:4][C:3]=1[O:27][CH2:28][CH2:29][CH2:30][N:31]([CH3:33])[CH3:32]

Participants

3

Reactant 2

HCID 48666329-aminobicyclo[3.3.1]nonane-9-carboxylic AcidHCID 667208756-{4-Chloro-3-[3-(dimethylamino)propoxy]phenyl}-5-(2,6-dimethoxyphenyl)pyridine-2-carboxylic acid

Product 1

HCID 667211449-({[6-{4-Chloro-3-[3-(dimethylamino)propoxy]phenyl}-5-(2,6-dimethoxyphenyl)pyridin-2-yl]carbonyl}amino)bicyclo[3.3.1]nonane-9-carboxylic acid hydrochlorideYield 77%

Procedure

According to the method described in example 1.8, starting from 400 mg (0.85 mmol) of 6-{4-chloro-3-[3-(dimethylamino)propoxy]phenyl}-5-(2,6-dimethoxyphenyl)pyridine-2-carboxylic acid and 218 mg (1.19 mmol) of 9-aminobicyclo[3.3.1]nonane-9-carboxylic acid and after reverse-phase purification and lyophilization, we obtain 220 mg of 9-({[6-{4-chloro-3-[3-(dimethylamino)propoxy]phenyl}-5-(2,6-dimethoxyphenyl)pyridin-2-yl]carbonyl}amino)bicyclo[3.3.1]nonane-9-carboxylic acid hydrochloride in the form of white powder.

Workup

  1. customafter reverse-phase purification and lyophilization, we

Sources & evidence

ORD record
ord-a615cda6f7e34b69b27b8598d81e5251
Source dataset
uspto-grants-2013_10
Patent number
US08552201B2

Reaction notes

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