Triethylamine → HCID 44128475, compound

HRID 1970630Notes

Reaction equation

HRID 1970630 reaction equation
[O:1]=[C:2]([N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1)[CH2:3][NH:4][C:5]([C:7]1[CH:11]=[C:10]([O:12][CH2:13][C:14]([N:16]2[CH2:20][CH2:19][CH2:18][C@H:17]2[C:21](=[O:27])[NH:22][CH:23]2[CH2:26][CH2:25][CH2:24]2)=[O:15])[N:9]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:8]=1)=[O:6].C(N(CC)CC)C.[CH3:47][O:48][CH2:49][CH2:50][O:51][C:52](Cl)=[O:53]>ClCCl>[CH3:47][O:48][CH2:49][CH2:50][O:51][C:52]([N:37]1[CH2:38][CH2:39][N:34]([C:2](=[O:1])[CH2:3][NH:4][C:5]([C:7]2[CH:11]=[C:10]([O:12][CH2:13][C:14]([N:16]3[CH2:20][CH2:19][CH2:18][C@H:17]3[C:21](=[O:27])[NH:22][CH:23]3[CH2:24][CH2:25][CH2:26]3)=[O:15])[N:9]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[N:8]=2)=[O:6])[CH2:35][CH2:36]1)=[O:53]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 694002-Methoxyethyl chloroformateHCID 66854863HCID 66854863, compound

Product 1

HCID 44128475HCID 44128475, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 100 mg 5-[2-((S)-2-Cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carboxylic acid (2-oxo-2-piperazin-1-yl-ethyl)-amide in 5 ml dichloromethane were added at 0° C. 56 l triethylamine and 24 l chloroformic acid 2-methoxyethyl ester. After stirring for 12 h it was concentrated and the residue obtained was purified by preparative HPLC (C18 reverse phase column, elution with a water/MeCN gradient with 0.1% TFA) to give the title compound.

Workup

  1. concentrationwas concentrated
  2. customthe residue obtained
  3. customwas purified by preparative HPLC (
  4. washC18 reverse phase column, elution with a water/MeCN gradient with 0.1% TFA)

Sources & evidence

ORD record
ord-cadd9e7958914b25883ffb0d6ec5978f
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

Loading…