Diisopropylethylamine → HCID 69767172, compound

HRID 1785255Notes

Reaction equation

HRID 1785255 reaction equation
[F:1][C:2]1([F:25])[CH2:6][CH2:5][C@@H:4]([C@@:7]([OH:24])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:8]([O:10][CH2:11][CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[O:9])[CH2:3]1.[ClH:26].[N:27]1([C:32](N)=[NH:33])C=CC=N1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[ClH:26].[F:25][C:2]1([F:1])[CH2:6][CH2:5][C@@H:4]([C@@:7]([OH:24])([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:8]([O:10][CH2:11][CH:12]2[CH2:17][CH2:16][N:15]([C:32](=[NH:27])[NH2:33])[CH2:14][CH2:13]2)=[O:9])[CH2:3]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2734672Pyrazole-1-carboxamidine monohydrochlorideHCID 69766026HCID 69766026, compound

Product 1

HCID 69767172HCID 69767172, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 14 mg of piperidin-4-ylmethyl (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoate in 0.020 ml of anhydrous dimethylformamide, 6.3 mg of 1H-pyrazole-1-carboxamidine hydrochloride and 0.008 ml of diisopropylethylamine were added, followed by stirring at room temperature for 12 hours. The reaction liquid was condensed and dried to solid. Thus obtained crude product was purified on silica gel column chromatography (eluent: chloroform/methanol =10/1), to provide 11 mg of the title compound in the form of a colorless solid.

Workup

  1. customThe reaction liquid
  2. customcondensed
  3. customdried to solid
  4. customThus obtained crude product
  5. customwas purified on silica gel column chromatography (eluent: chloroform/methanol =10/1)

Sources & evidence

ORD record
ord-56ac07f6175b4f60b76721db3706bd1f
Source dataset
uspto-grants-2009_03
Patent number
US07504432B2

Reaction notes

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