2-Aminoadamantane-2-carboxylic acid → HCID 66720864, compound

HRID 1040348Notes

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

Participants

Reactant 2

HCID 643542-Aminoadamantane-2-carboxylic acid

HCID 66720822HCID 66720822, compound

Product 1

HCID 66720864HCID 66720864, compoundYield 83.9%

Procedure

According to the saponification/peptide coupling steps described in examples 1.7 and 1.8 respectively, starting from 391 mg (0.91 mmol) of methyl 6-{4-chloro-3-[3-(dimethylamino)propoxy]phenyl}-5-(2-oxopyrrolidin-1-yl)pyridine-2-carboxylate and 265 mg (1.36 mmol) of 2-aminoadamantane-2-carboxylic acid, we obtain 241 mg of 2-({[6-{4-chloro-3-[3-(dimethylamino)propoxy]phenyl}-5-(2-oxopyrrolidin-1-yl)pyridin-2-yl]carbonyl}amino)adamantane-2-carboxylic acid hydrochloride in the form of white powder.

Sources & evidence

ORD record: ord-10785292efda4144819fe20a281fa8a7
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552201B2

Reaction notes

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