Isethionic Acid → 2-[5-(2,6-Dimethoxyphenyl)-1-[4-[N-methyl-N-(3-dimethylaminopropyl)carbamoyl]-2-isopropylphenyl]-3-pyrazolylcarbonylamino]-2-adamantanecarboxylic acid isethionate

HRID 582789

Reaction equation

HRID 582789 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[C:11]1[N:15]([C:16]2[CH:21]=[CH:20][C:19]([C:22](=[O:31])[N:23]([CH3:30])[CH2:24][CH2:25][CH2:26][N:27]([CH3:29])[CH3:28])=[CH:18][C:17]=2[CH:32]([CH3:34])[CH3:33])[N:14]=[C:13]([C:35]([NH:37][C:38]2([C:48]([OH:50])=[O:49])[CH:45]3[CH2:46][CH:41]4[CH2:42][CH:43]([CH2:47][CH:39]2[CH2:40]4)[CH2:44]3)=[O:36])[CH:12]=1.[S:51]([CH2:55][CH2:56][OH:57])([OH:54])(=[O:53])=[O:52]>CC(O)C>[S:51]([CH2:55][CH2:56][OH:57])([OH:54])(=[O:53])=[O:52].[CH3:10][O:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[C:11]1[N:15]([C:16]2[CH:21]=[CH:20][C:19]([C:22](=[O:31])[N:23]([CH3:30])[CH2:24][CH2:25][CH2:26][N:27]([CH3:28])[CH3:29])=[CH:18][C:17]=2[CH:32]([CH3:34])[CH3:33])[N:14]=[C:13]([C:35]([NH:37][C:38]2([C:48]([OH:50])=[O:49])[CH:39]3[CH2:40][CH:41]4[CH2:42][CH:43]([CH2:44][CH:45]2[CH2:46]4)[CH2:47]3)=[O:36])[CH:12]=1

Participants

4

Reactant 2

HCID 7866Isethionic AcidHCID 5311451SR142948A

Product 1

HCID 867542872-[5-(2,6-Dimethoxyphenyl)-1-[4-[N-methyl-N-(3-dimethylaminopropyl)carbamoyl]-2-isopropylphenyl]-3-pyrazolylcarbonylamino]-2-adamantanecarboxylic acid isethionateYield 46.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 0.1 g of the compound obtained in EXAMPLE 1' in 3 ml of 2-propanol is heated to reflux, 0.022 g of 83% isethionic acid (obtained by elution of sodium isethionate on DOWEX® 50 W×8 resin in H+ form) is added and crystallization is allowed to take place overnight. The crystallized product formed is drained. 0.055 g of the expected product is obtained, m.p.=230° C.

Workup

  1. temperatureis heated
  2. temperatureto reflux
  3. customcrystallization
  4. customThe crystallized product formed

Sources & evidence

ORD record
ord-0315a2a4f4e44e0691efe2780235ac73
Source dataset
uspto-grants-1999_07
Patent number
US05925661

Linked notes

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