Diisopropylethylamine → HCID 67331064, compound

HRID 1896795Notes

Reaction equation

HRID 1896795 reaction equation
[F:1][C:2]([F:8])([F:7])[CH2:3][C:4](O)=[O:5].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:42]1([C:48]2[O:49][C:50]3[CH:56]=[CH:55][C:54]([NH2:57])=[CH:53][C:51]=3[CH:52]=2)[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>ClCCl.C(OCC)(=O)C>[C:42]1([C:48]2[O:49][C:50]3[CH:56]=[CH:55][C:54]([NH:57][C:4](=[O:5])[CH2:3][C:2]([F:8])([F:7])[F:1])=[CH:53][C:51]=3[CH:52]=2)[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 27779723,3,3-Trifluoropropionic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 167651722-Phenyl-1-benzofuran-5-amine

Product 1

HCID 67331064HCID 67331064, compoundYield 29.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 3,3,3-trifluoropropanoic acid (136 mg, 1.06 mmol) in dry dichloromethane (10 mL) was added HATU (468 mg, 1.23 mmol) and diisopropylethylamine (580 μL, 3.35 mmol). The mixture was then stirred at room temperature for 10 min. 2-phenylbenzofuran-5-amine (234 mg, 1.12 mmol) was then added and the resulting mixture was stirred at room temperature for 48 h. Ethyl acetate was added and the organic layer was washed once with saturated aqueous water. The combined organic layers were dried over anhydrous MgSO4 and evaporated. The resulting solid was purified by column chromatography eluting using a gradient (ethyl acetate/hexanes 1:3 v/v to ethyl acetate/hexanes 1:1 v/v) followed by trituration in ethyl acetate to afford 99.3 mg (28%) of the title compound (LCMS RT=6.62 min)

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 48 h
  2. washthe organic layer was washed once with saturated aqueous water
  3. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  4. customevaporated
  5. customThe resulting solid was purified by column chromatography
  6. washeluting

Sources & evidence

ORD record
ord-07da71ba7d574f3cbd8def2a87ffe4a8
Source dataset
uspto-grants-2013_08
Patent number
US08518980B2

Reaction notes

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