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Triethylamine → Ethyl (1R*,2R*)-2-{4-cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl}cyclopropanecarboxylate

HRID 17509
ノート
印刷プレビュー

反応式

HRID 17509 の反応式
[C:1]([C:3]1[C:8]2[N:9]=[C:10]([C@@H:12]3[CH2:14][C@H:13]3[C:15]([O:17][CH2:18][CH3:19])=[O:16])[O:11][C:7]=2[C:6](F)=[C:5]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:4]=1[CH3:27])#[N:2].C(N(CC)CC)C.[CH3:35][N:36]([CH3:42])[C@H:37]1[CH2:41][CH2:40][NH:39][CH2:38]1>CS(C)=O>[C:1]([C:3]1[C:8]2[N:9]=[C:10]([C@@H:12]3[CH2:14][C@H:13]3[C:15]([O:17][CH2:18][CH3:19])=[O:16])[O:11][C:7]=2[C:6]([N:39]2[CH2:40][CH2:41][C@H:37]([N:36]([CH3:42])[CH3:35])[CH2:38]2)=[C:5]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:4]=1[CH3:27])#[N:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 86630862Ethyl (1R*,2R*)-2-[4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-yl]cyclopropanecarboxylate

生成物 1

HCID 86630861Ethyl (1R*,2R*)-2-{4-cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl}cyclopropanecarboxylate収率 42%

試薬・触媒・溶媒 1

HCID 679
Dimethyl Sulfoxide
溶媒

反応条件

温度
95 °C

実験手順

Ethyl (1R*,2R*)-2-[4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-yl]cyclopropanecarboxylate (I-216) (200 mg, 0.55 mmol) was dissolved in dimethyl sulfoxide (5 ml), then triethylamine (146 μl, 1.10 mmol) and (3S)-3-(dimethylamino)pyrrolidine (146 μl, 1.15 mmol) were added, followed by stirring at 95° C. for 4 hours. After cooled, this was concentrated under reduced pressure, diluted with chloroform, and 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 subjected to preparative TLC. The eluate with chloroform/methanol (5:1, v/v) gave the entitled compound (105 mg, 42%) as a red brown solid.

後処理

  1. temperatureAfter cooled
  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

出典と根拠

ORDレコード
ord-5fd2e993019f4c2ea0af983b8846a64f
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07737166B2

反応ノート

読み込み中…

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