Triethylamine → HCID 51041904, compound

HRID 17597Notes

Reaction equation

HRID 17597 reaction equation
[CH:1]1([C:4]2[O:5][C:6]3[C:7](=[C:9]([C:20]#[N:21])[C:10]([CH3:19])=[C:11]([C:14]4[S:15][CH:16]=[CH:17][CH:18]=4)[C:12]=3F)[N:8]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:29][N:30]([CH3:36])[C@H:31]1[CH2:35][CH2:34][NH:33][CH2:32]1.C(OCC)(=O)C>CS(C)=O.[Cl-].[Na+].O>[CH:1]1([C:4]2[O:5][C:6]3[C:7](=[C:9]([C:20]#[N:21])[C:10]([CH3:19])=[C:11]([C:14]4[S:15][CH:16]=[CH:17][CH:18]=4)[C:12]=3[N:33]3[CH2:34][CH2:35][C@H:31]([N:30]([CH3:36])[CH3:29])[CH2:32]3)[N:8]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 685859762-Cyclopropyl-7-fluoro-5-methyl-6-(thiophen-2-yl)-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 51041904HCID 51041904, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
90 °C

Procedure

2-Cyclopropyl-7-fluoro-5-methyl-6-(thiophen-2-yl)-1,3-benzoxazole-4-carbonitrile (I-307) (192 mg, 0.64 mmol) was dissolved in dimethyl sulfoxide (4 ml), and at room temperature, triethylamine (117 μl, 0.84 mmol) and (3S)-3-(dimethylamino)pyrrolidine (106 μl, 0.84 mmol) was added. After stirred under nitrogen atmosphere at 90° C. for 12.5 hours, this was cooled to room temperature. The reaction liquid was fractionated with ethyl acetate and saturated brine. The aqueous layer was further extracted twice with ethyl acetate. The organic layers were combined, washed with saturated brine, then dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, then the solvent was evaporated away, and the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=93:7, v/v) to obtain the entitled compound (208 mg, 83%) as a pale brown solid.

Workup

  1. temperaturethis was cooled to room temperature
  2. customThe reaction liquid
  3. extractionThe aqueous layer was further extracted twice with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe insoluble matter was separated by filtration
  7. customthe solvent was evaporated away
  8. customthe resulting residue was purified by preparative TLC (eluent, chloroform

Sources & evidence

ORD record
ord-ae837be6330643bdaff9b1fbe655a198
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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