Triethylamine → HCID 51039312, compound

HRID 17361Notes

Reaction equation

HRID 17361 reaction equation
F[C:2]1[C:3]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:4]([CH3:18])[C:5]([C:16]#[N:17])=[C:6]2[C:10]=1[O:9][C:8]([C:11]1[O:12][CH:13]=[CH:14][CH:15]=1)=[N:7]2.C(N(CC)CC)C.[CH3:32][N:33]([CH3:39])[C@H:34]1[CH2:38][CH2:37][NH:36][CH2:35]1.C(OCC)(=O)C>CS(C)=O.[Cl-].[Na+].O>[CH3:32][N:33]([CH3:39])[C@H:34]1[CH2:38][CH2:37][N:36]([C:2]2[C:3]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:4]([CH3:18])[C:5]([C:16]#[N:17])=[C:6]3[C:10]=2[O:9][C:8]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)=[N:7]3)[CH2:35]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 685850137-Fluoro-2-(2-furyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 51039312HCID 51039312, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
90 °C

Procedure

7-Fluoro-2-(2-furyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-105) (40 mg, 0.13 mmol) was dissolved in anhydrous dimethyl sulfoxide (2 ml), and at room temperature, triethylamine (26 μl, 0.19 mmol) and (3S)-3-(dimethylamino)pyrrolidine (21 μl, 0.16 mmol) were added. This mixture liquid was stirred at 90° C. for 11 hours, then cooled to room temperature. This was fractionated with ethyl acetate and saturated brine. The aqueous layer was separated, and this was extracted twice with ethyl acetate.

Workup

  1. temperaturecooled to room temperature
  2. customThe aqueous layer was separated
  3. extractionthis was extracted twice with ethyl acetate

Sources & evidence

ORD record
ord-481576c250af446b9a24de058d7cc36c
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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