2-Aminoadamantane-2-carboxylic acid → HCID 66720820, compound

HRID 1639908Notes

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[Cl: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:43]([OH:45])=[O:44])[CH:40]2[CH2:41][CH:36]3[CH2:37][CH:38]([CH2:42][CH:34]1[CH2:35]3)[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:32][C:33]3([C:43]([OH:45])=[O:44])[CH:40]4[CH2:39][CH:38]5[CH2:37][CH:36]([CH2:35][CH:34]3[CH2:42]5)[CH2:41]4)=[O:15])[CH:11]=[CH:10][C:9]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])=[CH:4][C:3]=1[O:25][CH2:26][CH2:27][CH2:28][N:29]([CH3:30])[CH3:31]

Participants

Reactant 2

HCID 643542-Aminoadamantane-2-carboxylic acid

HCID 66721005HCID 66721005, compound

Product 1

HCID 66720820HCID 66720820, compoundYield 57.8%

Procedure

According to the saponification/peptide coupling steps described in examples 1.7 and 1.8 respectively, starting from 290 mg (0.63 mmol) of methyl 6-{4-chloro-3-[3-(dimethylamino)propoxy]phenyl}-5-(2-chlorophenyl)pyridine-2-carboxylate and 184 mg (0.94 mmol) of 2-aminoadamantane-2-carboxylic acid, we obtain 120 mg of 2-({[6-{4-chloro-3-[3-(dimethylamino)propoxy]phenyl}-5-(2-chlorophenyl)pyridin-2-yl]carbonyl}amino)adamantane-2-carboxylic acid hydrochloride in the form of white powder.

Sources & evidence

ORD record: ord-a33372dce1884b1e8b2730044c901048
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08110579B2

Reaction notes

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