Diisopropylethylamine → HCID 44227499, compound

HRID 1914578Notes

Reaction equation

HRID 1914578 reaction equation
[O:1]1[CH:10]2[CH:5]([NH:6][CH2:7][CH2:8][CH2:9]2)[O:4][CH2:3][CH2:2]1.[NH:11]1[CH:15]=[C:14]([C:16]2[S:20][CH:19]=[C:18]([C:21](O)=[O:22])[CH:17]=2)[CH:13]=[N:12]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(#N)C>[O:4]1[CH:9]2[CH:10]([CH2:5][N:6]([C:21]([C:18]3[CH:17]=[C:16]([C:14]4[CH:15]=[N:11][NH:12][CH:13]=4)[S:20][CH:19]=3)=[O:22])[CH2:7][CH2:8]2)[O:1][CH2:2][CH2:3]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 55299474HCID 55299474, compoundHCID 581101935-(1H-Pyrazol-4-YL)thiophene-3-carboxylic acid

Product 1

HCID 44227499HCID 44227499, compoundYield 8.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Octahydro-[1,4]dioxino[2,3-b]pyridine (0.049 g, 0.34 mmol) was dissolved in acetonitrile (1 mL) then 5-(1H-pyrazol-4-yl)-thiophene-3-carboxylic acid (0.060 g, 0.31 mmol) was added then DIPEA (0.116 mL, 0.68 mmol) followed by HATU (0.141 g, 0.37 mmol). The resulting mixture was stirred overnight then further amounts of DIPEA (0.31 mmol) and HATU (0.31 mmol) were added and stirring continued overnight. The mixture was evaporated and the residue was suspended in sodium hydroxide (1 N, 2.5 mL) and stirred for 20 minutes. The mixture was extracted with DCM (×3) then 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) over 20 minutes and the fractions containing the desired product were combined and freeze-dried to give the title compound as a white foam (0.008 g). LCMS m/z 320.19 [M+H]+ R.T.=5.95 min (Analytical Method 2).

Workup

  1. stirringstirring continued overnight
  2. customThe mixture was evaporated
  3. stirringstirred for 20 minutes
  4. extractionThe mixture was extracted with DCM (×3)
  5. dry with materialthe organics were dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe material was purified by HPLC
  9. washeluting with 5%-95% acetonitrile in water (0.1% formic acid) over 20 minutes
  10. additionthe fractions containing the desired product
  11. customfreeze-dried

Sources & evidence

ORD record
ord-7ce16191d291469dab3c83a8446e2d1b
Source dataset
uspto-grants-2013_12
Patent number
US08614209B2

Reaction notes

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