2-Aminoadamantane-2-carboxylic acid → 2-{[1-(5-Isoquinolyl)-5-(2,6-dimethoxyphenyl)-3-pyrazolyl]carbonylamino}-2-adamantanecarboxylic acid

HRID 975129Notes

Reaction equation

HRID 975129 reaction equation
[NH2:1][C:2]1([C:12]([OH:14])=[O:13])[CH:9]2[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2.[CH:15]1[C:24]2[C:19](=[C:20]([N:25]3[C:29]([C:30]4[C:35]([O:36][CH3:37])=[CH:34][CH:33]=[CH:32][C:31]=4[O:38][CH3:39])=[CH:28][C:27]([C:40](Cl)=[O:41])=[N:26]3)[CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][N:16]=1>N1C=CC=CC=1.ClCCl>[CH:15]1[C:24]2[C:19](=[C:20]([N:25]3[C:29]([C:30]4[C:31]([O:38][CH3:39])=[CH:32][CH:33]=[CH:34][C:35]=4[O:36][CH3:37])=[CH:28][C:27]([C:40]([NH:1][C:2]4([C:12]([OH:14])=[O:13])[CH:9]5[CH2:8][CH:7]6[CH2:6][CH:5]([CH2:4][CH:3]4[CH2:11]6)[CH2:10]5)=[O:41])=[N:26]3)[CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][N:16]=1

Participants

5

Reactant 2

HCID 643542-Aminoadamantane-2-carboxylic acidHCID 189266581-(5-Isoquinolyl)-5-(2,6-dimethoxyphenyl)-3-pyrazolecarbonyl chloride

Product 1

HCID 189266552-{[1-(5-Isoquinolyl)-5-(2,6-dimethoxyphenyl)-3-pyrazolyl]carbonylamino}-2-adamantanecarboxylic acid

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

0.75 g of 2-amino-2-adamantanecarboxylic acid is dissolved in 20 ml of pyridine. 1.4 g of 1-(5-isoquinolyl)-5-(2,6-dimethoxyphenyl)-3-pyrazolecarbonyl chloride, dissolved in 20 ml of dichloromethane, are added and the reaction mixture is left overnight at room temperature. It is concentrated under vacuum, the residue is taken up with pH 2 buffer, the mixture is stirred and the precipitate is filtered off and rinsed with diisopropyl ether.

Workup

  1. additionare added
  2. concentrationIt is concentrated under vacuum
  3. filtrationthe precipitate is filtered off
  4. washrinsed with diisopropyl ether

Sources & evidence

ORD record
ord-b0f85f2830a34baa9f603524b64045e2
Source dataset
uspto-grants-1997_03
Patent number
US05607958

Reaction notes

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