Diisopropylethylamine → HCID 68520373, compound

HRID 1863949Notes

Reaction equation

HRID 1863949 reaction equation
Br[CH2:2][CH2:3][CH2:4][NH:5][C:6]([C:8]1[NH:12][N:11]=[C:10]([C:13]([F:16])([F:15])[F:14])[CH:9]=1)=[O:7].C(N(CC)C(C)C)(C)C>C(#N)C>[F:14][C:13]([F:16])([F:15])[C:10]1[CH:9]=[C:8]2[C:6](=[O:7])[NH:5][CH2:4][CH2:3][CH2:2][N:12]2[N:11]=1

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 178523266HCID 178523266, compound

Product 1

HCID 68520373HCID 68520373, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 400 mg (1.33 mmol) of N-(3-bromopropyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide, 350 mL (2 mmol) of N,N-diisopropylethylamine, and 8 mL of acetonitrile was stirred at reflux for 4.5 h. The cooled reaction mixture was concentrated, and the residue was flash chromatographed on silica gel [0-10% of (9:1 methanol:concentrated ammonium hydroxide) in dichloromethane]. Further purification by preparative HPLC (C18 reverse phase column, 10-50% acetonitrile in water containing 0.05% trifluoroacetic acid) separated the product from a major by-product, 2-[3-(trifluoromethyl)-1H-pyrazol-5-yl]-1,3-oxazinane, to give the title compound.

Workup

  1. temperatureat reflux for 4.5 h
  2. customThe cooled reaction mixture
  3. concentrationwas concentrated
  4. customchromatographed on silica gel [0-10% of (9:1 methanol:concentrated ammonium hydroxide) in dichloromethane]
  5. customFurther purification by preparative HPLC (C18 reverse phase column, 10-50% acetonitrile in water containing 0.05% trifluoroacetic acid)
  6. customseparated the product from a major by-product, 2-[3-(trifluoromethyl)-1H-pyrazol-5-yl]-1,3-oxazinane

Sources & evidence

ORD record
ord-0dbb4b0e56714451b9c65e6207ff7bfe
Source dataset
uspto-grants-2009_12
Patent number
US07625888B2

Reaction notes

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