2-Aminoadamantane-2-carboxylic acid → HCID 66720978, compound

HRID 1040340Notes

Reaction equation

HRID 1040340 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14](OCC)=[O:15])[CH:11]=[CH:10][C:9]=2[C:19]2[C:24]([O:25][CH3:26])=[CH:23][CH:22]=[CH:21][C:20]=2[O:27][CH3:28])=[CH:4][C:3]=1[O:29][CH:30]1C[CH2:33][N:32]([CH3:35])[CH2:31]1.[NH2:36][C:37]1([C:47]([OH:49])=[O:48])[CH:44]2[CH2:45][CH:40]3[CH2:41][CH:42]([CH2:46][CH:38]1[CH2:39]3)[CH2:43]2>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14]([NH:36][C:37]3([C:47]([OH:49])=[O:48])[CH:44]4[CH2:43][CH:42]5[CH2:41][CH:40]([CH2:39][CH:38]3[CH2:46]5)[CH2:45]4)=[O:15])[CH:11]=[CH:10][C:9]=2[C:19]2[C:20]([O:27][CH3:28])=[CH:21][CH:22]=[CH:23][C:24]=2[O:25][CH3:26])=[CH:4][C:3]=1[O:29][CH2:30][CH2:31][N:32]([CH3:35])[CH3:33]

Participants

3

Reactant 2

HCID 643542-Aminoadamantane-2-carboxylic acidHCID 66720745Ethyl 6-{4-chloro-3-[(1-methylpyrrolidin-3-yl)oxy]phenyl}-5-(2,6-dimethoxyphenyl)pyridine-2-carboxylate

Product 1

HCID 66720978HCID 66720978, compoundYield 50.5%

Procedure

According to the saponification/peptide coupling steps described in examples 1.7 and 1.8 respectively, starting from 250 mg (0.5 mmol) of ethyl 6-{4-chloro-3-[(1-methylpyrrolidin-3-yl)oxy]phenyl}-5-(2,6-dimethoxyphenyl)pyridine-2-carboxylate and 100 mg (0.51 mmol) of 2-aminoadamantane-2-carboxylic acid, we obtain 160 mg of 2-({[6-{4-chloro-3-[2-(dimethylamino)ethoxy]phenyl}-5-(2,6-dimethoxyphenyl)pyridin-2-yl]carbonyl}amino)adamantane-2-carboxylic acid in the form of white powder.

Sources & evidence

ORD record
ord-dea8aed360604863bb288b679a2cd5f4
Source dataset
uspto-grants-2013_10
Patent number
US08552201B2

Reaction notes

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