Diisopropylethylamine → HCID 86655236, compound

HRID 1256166Notes

Reaction equation

HRID 1256166 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]([NH:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13]([OH:15])=O)[CH:9]=[CH:10][CH:11]=1)=[O:4].[CH2:18]([NH2:21])[C:19]#[CH:20].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(#N)C>[F:16][C:2]([F:1])([F:17])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][C:13](=[O:15])[NH:21][CH2:18][C:19]#[CH:20])[CH:7]=1)=[O:4]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 239041PropargylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 65345839HCID 65345839, compound

Product 1

HCID 86655236HCID 86655236, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To the mixture of 2-(3-(2,2,2-trifluoroacetamido)phenyl)acetic acid (2.96 g, 12 mmol), propargylamine (0.97 ml, 15 mmol), HATU (4.5 g, 12 mmol) in acetonitrile (50 ml), added DIPEA (5.2 ml, 30 mmol) slowly. Stirring was kept 2 hours at room temperature. Removed solvent, extracted with EtOAc, washed with 1N HCl, water and brine, dried over sodium sulfate. Concentrated to get 1.42 g 2,2,2-trifluoro-N-(3-(2-oxo-2-(prop-2-ynylamino)ethyl)phenyl)acetamide as white solid.

Workup

  1. extractionRemoved solvent, extracted with EtOAc
  2. washwashed with 1N HCl, water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationConcentrated

Sources & evidence

ORD record
ord-b003dcba8bf54bcdbb68fa02442de5b2
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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