Pyridine → HCID 44128472, compound

HRID 1970626Notes

Reaction equation

HRID 1970626 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].N1C=CC=CC=1.[C:46](Cl)(=[O:51])[CH2:47][CH2:48][CH2:49][CH3:50]>ClCCl.CN(C1C=CN=CC=1)C>[O:1]=[C:2]([N:34]1[CH2:39][CH2:38][N:37]([C:46](=[O:51])[CH2:47][CH2:48][CH2:49][CH3:50])[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[CH2:24][CH2:25][CH2:26]2)=[O:15])[N:9]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:8]=1)=[O:6]

Participants

6

Reactant 3

HCID 1049PyridineHCID 61186Valeryl chlorideHCID 66854863HCID 66854863, compound

Product 1

HCID 44128472HCID 44128472, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 50 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 4 ml dichloromethane were added at 0° C. 15 l pyridine, 13 l valeryl chloride and a catalytic amount of DMAP. 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-c5350ae8fc4e410abdc0697f20ebeec9
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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