Diisopropylethylamine → HCID 58007534, compound

HRID 1094382Notes

Reaction equation

HRID 1094382 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[CH:3]=1.C(N(CC)C(C)C)(C)C.[C:18]([C:26](Cl)=[O:27])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1COCC1.CC(OC)(C)C>[CH3:7][N:6]1[C:2]([NH:1][C:26](=[O:27])[C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:3][C:4]([CH3:8])=[N:5]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 5207211,3-Dimethyl-1H-pyrazol-5-amineHCID 110842942-Oxo-2-phenylacetyl chloride

Product 1

HCID 58007534HCID 58007534, compoundYield 48.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To a solution of 5-amino-1,3-dimethylpyrazole (2.00 g, 18.0 mmol) in THF (20 mL) was added at ambient temperature N,N-diisopropyl ethyl amine (4.62 mL, 27.0 mmol) and over a period of 5 min benzoylformic acid chloride (which might be prepared according to Synlett (11) 1763-1765, 1999, 3.64 g, 21.6 mmol) and the reaction mixture was stirred for 18 h at this temperature. It was diluted with TBME (50 mL) and washed twice with water (50 mL) and brine (50 mL). The combined aqueous layers were extracted with TBME (50 mL) and the combined organic layers were dried over sodium sulfate. Concentration and purification by chromatography (SiO2, heptane:ethyl acetate=50:50 to 0:100) afforded the title compound (2.11 g, 48%) as a light brown oil. MS m/e: 244.3 [M+H]+.

Workup

  1. washwashed twice with water (50 mL) and brine (50 mL)
  2. extractionThe combined aqueous layers were extracted with TBME (50 mL)
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. concentrationConcentration and purification by chromatography (SiO2, heptane:ethyl acetate=50:50 to 0:100)

Sources & evidence

ORD record
ord-6708317a247f4f5589c080469f4a74b3
Source dataset
uspto-grants-2012_03
Patent number
US08133909B2

Reaction notes

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