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

HRID 17579ノート

反応式

HRID 17579 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
95 °C

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-69d1776668eb40508be5cabbba3a1dfd
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

反応ノート

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