Diisopropylethylamine → HCID 44227500, compound

HRID 1914576Notes

Reaction equation

HRID 1914576 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.CCN(C(C)C)C(C)C.[F:23][C:24]([F:37])([F:36])[CH2:25][N:26]1[CH:35]2[CH:30]([CH2:31][CH2:32][CH2:33][CH2:34]2)[NH:29][CH2:28][CH2:27]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(#N)C>[NH:2]1[CH:3]=[C:4]([C:6]2[S:10][CH:9]=[C:8]([C:11]([N:29]3[CH:30]4[CH:35]([CH2:34][CH2:33][CH2:32][CH2:31]4)[N:26]([CH2:25][C:24]([F:36])([F:37])[F:23])[CH2:27][CH2:28]3)=[O:13])[CH:7]=2)[CH:5]=[N:1]1

Participants

6

Reactant 4

HCID 81531Diisopropylethylamine2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2×HCID 581101935-(1H-Pyrazol-4-YL)thiophene-3-carboxylic acidHCID 58110330HCID 58110330, compound

Product 1

HCID 44227500HCID 44227500, compoundYield 12.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-(1H-Pyrazol-4-yl)-thiophene-3-carboxylic acid (0.080 g, 0.41 mmol) was suspended in acetonitrile (2 mL) then DIPEA (0.158 mL, 0.90 mmol) and 1-(2,2,2-trifluoro-ethyl)-decahydro-quinoxaline (0.119 g, 0.54 mmol) were added followed by HATU (0.192 g, 0.50 mmol). The resulting mixture was stirred for about 24 hours and then further amounts of DIPEA (79 μL) and HATU (0.192 g) were added and stirring continued over the weekend. The mixture was evaporated and the residue was taken up in sodium hydroxide (1 N) and stirred for 30 minutes. HCl (1 N, 2.5 mL) was added and the solution extracted with ethyl acetate (×3). The organics were dried over sodium sulfate, filtered and evaporated. The material was purified by HPLC, eluting with 5%-95% acetonitrile in water (0.1% formic acid) and the fractions containing the desired product were combined and freeze-dried to give the title compound as a white solid (0.020 g). LCMS m/z 399.17 [M+H]+ R.T.=10.05 min (Analytical Method 2).

Workup

  1. stirringstirring
  2. customThe mixture was evaporated
  3. stirringstirred for 30 minutes
  4. additionHCl (1 N, 2.5 mL) was added
  5. extractionthe solution extracted with ethyl acetate (×3)
  6. dry with materialThe organics were dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe material was purified by HPLC
  10. washeluting with 5%-95% acetonitrile in water (0.1% formic acid)
  11. additionthe fractions containing the desired product
  12. customfreeze-dried

Sources & evidence

ORD record
ord-ffd1ba6003874fe889eb0fe411216b5d
Source dataset
uspto-grants-2013_12
Patent number
US08614209B2

Reaction notes

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