Triethylamine → 2-Cyclopentene 7-[(3S)-3-(dimethylamino)pyrrolidinyl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17563Notes

Reaction equation

HRID 17563 reaction equation
[CH:1]1([C:6]2[O:7][C:8]3[C:9](=[C:11]([C:23]#[N:24])[C:12]([CH3:22])=[C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:14]=3F)[N:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:32][N:33]([CH3:39])[C@H:34]1[CH2:38][CH2:37][NH:36][CH2:35]1>CS(C)=O>[CH2:5]1[CH2:4][CH2:3][CH:2]=[CH:1]1.[CH3:32][N:33]([CH3:39])[C@H:34]1[CH2:38][CH2:37][N:36]([C:14]2[C:13]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[C:12]([CH3:22])[C:11]([C:23]#[N:24])=[C:9]3[C:8]=2[O:7][CH:6]=[N:10]3)[CH2:35]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 68584553HCID 68584553, compound

Product 1

HCID 685845192-Cyclopentene 7-[(3S)-3-(dimethylamino)pyrrolidinyl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrileYield 48.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
95 °C

Procedure

2-Cyclopentyl-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-275) (112 mg, 0.24 mmol) was dissolved in dimethyl sulfoxide (5 ml), then triethylamine (100 μl, 0.36 mmol) and (3S)-3-(dimethylamino)pyrrolidine (93 μl, 0.31 mmol) were added, followed by stirring under nitrogen atmosphere at 95° C. for 4 hours. After cooling, this was concentrated under reduced pressure, diluted, with chloroform, washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, then the solvent was evaporated away under reduced pressure. The resulting residue was purified by preparative TLC (chloroform:methanol=10:1, v/v) to obtain the entitled compound (48 mg, 33%) as a white crystal.

Workup

  1. temperatureAfter cooling
  2. concentrationthis was concentrated under reduced pressure
  3. additiondiluted, with chloroform
  4. washwashed with saturated brine
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated away under reduced pressure
  7. customThe resulting residue was purified by preparative TLC (chloroform

Sources & evidence

ORD record
ord-334bb5a5aad149789297e7ea2d3768b7
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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