2-Aminoadamantane-2-carboxylic acid → HCID 66720754, compound

HRID 1639907Notes

Reaction equation

HRID 1639907 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)=[CH:12][CH:11]=[C:10]([C:20](OC)=[O:21])[N:9]=2)=[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[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)=[CH:12][CH:11]=[C:10]([C:20]([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:21])[N:9]=2)=[CH:4][C:3]=1[O:24][CH2:25][CH2:26][CH2:27][N:28]([CH3:30])[CH3:29]

Participants

3

Reactant 2

HCID 643542-Aminoadamantane-2-carboxylic acidHCID 66720731HCID 66720731, compound

Product 1

HCID 66720754HCID 66720754, compoundYield 102.3%

Procedure

According to the saponification/peptide coupling steps described in examples 1.7 and 1.8 respectively, starting from 581 mg (1.36 mmol) of methyl 2′-{4-chloro-3-[3-(dimethylamino)propoxy]phenyl}-2,3′-bipyridine-6′-carboxylate and 365 mg (1.87 mmol) of 2-aminoadamantane-2-carboxylic acid, we obtain 435 mg of 2-{[(2′-{4-chloro-3-[3-(dimethylamino)propoxy]phenyl}-2,3′-bipyridin-6′-yl)carbonyl]amino}adamantane-2-carboxylic acid hydrochloride in the form of white powder.

Sources & evidence

ORD record
ord-b9ed6085d0af43d6b4d63f98eba2dc4f
Source dataset
uspto-grants-2012_02
Patent number
US08110579B2

Reaction notes

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