Triethylamine → 2-cyclopropyl-7-[(3S)-3-(ethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17579Notes

Reaction equation

HRID 17579 reaction equation
[CH2:1]([NH:3][C@H:4]1[CH2:8][CH2:7][NH:6][CH2:5]1)[CH3:2].C(N(CC)CC)C.[CH:16]1([C:19]2[O:20][C:21]3[C:22](=[C:24]([C:36]#[N:37])[C:25]([CH3:35])=[C:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C:27]=3F)[N:23]=2)[CH2:18][CH2:17]1>CS(C)=O>[CH:16]1([C:19]2[O:20][C:21]3[C:22](=[C:24]([C:36]#[N:37])[C:25]([CH3:35])=[C:26]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:27]=3[N:6]3[CH2:7][CH2:8][C@H:4]([NH:3][CH2:1][CH3:2])[CH2:5]3)[N:23]=2)[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 22831501(3S)-(-)-3-(Ethylamino)pyrrolidineHCID 510414282-Cyclopropyl-7-fluoro-5-methyl-6-phenylbenzoxazole-4-carbonitrile

Product 1

HCID 685844372-cyclopropyl-7-[(3S)-3-(ethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrileYield 23.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
95 °C

Procedure

(3S)-3-(Ethylamino)pyrrolidine (85 μl, 0.684 mmol) and triethylamine (95 μl, 0.684 mmol) were added to a dimethyl sulfoxide (2 ml) solution of 2-cyclopropyl-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-173) (100 mg, 0.342 mmol), followed by stirring in an oil bath at 95° C. for 3 hours. The reaction liquid was concentrated under reduced pressure, then the residue was dissolved in ethyl acetate, and washed with water and saturated brine. After drying over anhydrous sodium sulfate, the insoluble matter was separated by filtration, and the residue obtained by concentration was purified by preparative TLC (eluent, chloroform:methanol=10:1, v/v), and the obtained eluate was purified in slurry with isopropyl ether to obtain the entitled compound (31.0 mg, 23%) as a white solid.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with water and saturated brine
  5. dry with materialAfter drying over anhydrous sodium sulfate
  6. customthe insoluble matter was separated by filtration
  7. customthe residue obtained by concentration
  8. customwas purified by preparative TLC (eluent, chloroform
  9. custommethanol=10:1, v/v), and the obtained eluate was purified in slurry with isopropyl ether

Sources & evidence

ORD record
ord-69d1776668eb40508be5cabbba3a1dfd
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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