Diisopropylethylamine → HCID 67059908, compound

HRID 238254Notes

Reaction equation

HRID 238254 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[S:10][CH:9]=[C:8]([C:11]([OH:13])=O)[CH:7]=2)[CH:3]=[N:2]1.[C:14]1([C:20]2([OH:26])[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>C(#N)C>[OH:26][C:20]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:25][CH2:24][N:23]([C:11]([C:8]2[CH:7]=[C:6]([C:4]3[CH:5]=[N:1][NH:2][CH:3]=3)[S:10][CH:9]=2)=[O:13])[CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 963874-Phenylpiperidin-4-olHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 581101935-(1H-Pyrazol-4-YL)thiophene-3-carboxylic acid

Product 1

HCID 67059908HCID 67059908, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-(1H-Pyrazol-4-yl)-thiophene-3-carboxylic acid (0.04 g, 0.2 mmol) and 4-phenyl-piperidin-4-ol (0.041 g, 0.23 mmol) were dissolved in acetonitrile (3 mL). HATU (0.24 mmol) and diisopropylethylamine (0.077 mL, 0.45 mmol) were added and the reaction mixture was stirred. After 1 hour the solvent was evaporated under vacuum and the residue stirred with aqueous sodium hydroxide (1 N, 3 mL) for 0.5 hours. The mixture was diluted with ethyl acetate and washed with brine, dried over magnesium sulphate, filtered and the solvent evaporated under vacuum. The residue was purified by flash chromatography on silica eluting with ethyl acetate. The fractions containing the desired product were concentrated under vacuum to give the title compound (0.041 g) as a white solid.

Workup

  1. customAfter 1 hour the solvent was evaporated under vacuum
  2. stirringthe residue stirred with aqueous sodium hydroxide (1 N, 3 mL) for 0.5 hours
  3. additionThe mixture was diluted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customthe solvent evaporated under vacuum
  8. customThe residue was purified by flash chromatography on silica eluting with ethyl acetate
  9. additionThe fractions containing the desired product
  10. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-bf876694b5b24ef1ac2ecf1037f324c5
Source dataset
uspto-grants-2014_02
Patent number
US08642621B2

Reaction notes

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