Triethylamine → HCID 86630853、化合物

HRID 17479ノート

反応式

HRID 17479 の反応式
[C:1]([C:3]1[C:8]2[N:9]=[C:10]([N:12]3[CH2:15][CH:14]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13]3)[O:11][C:7]=2[C:6](F)=[C:5]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:4]=1[CH3:29])#[N:2].C(N(CC)CC)C.[CH3:37][N:38]([CH3:44])[C@H:39]1[CH2:43][CH2:42][NH:41][CH2:40]1>CS(C)=O>[C:1]([C:3]1[C:8]2[N:9]=[C:10]([N:12]3[CH2:15][CH:14]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13]3)[O:11][C:7]=2[C:6]([N:41]2[CH2:42][CH2:43][C@H:39]([N:38]([CH3:44])[CH3:37])[CH2:40]2)=[C:5]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:4]=1[CH3:29])#[N:2]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 86630854Ethyl [1-(4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)azetidin-3-yl]acetate

生成物 1

HCID 86630853HCID 86630853、化合物収率 41.4%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
150 °C

実験手順

Ethyl [1-(4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)azetidin-3-yl]acetate (I-190) (428 mg, 1.09 mmol) was dissolved in dimethyl sulfoxide (10 ml), then triethylamine (312 μl, 2.18 mmol) and (3S)-3-(dimethylamino)pyrrolidine (290 μl, 2.29 mmol) were added, followed by stirring in a sealed tube at 150° C. for 6 hours. After cooling, concentration under reduced pressure, dilution with chloroform, and washing with water, the organic layer was dried over anhydrous magnesium sulfate, then the solvent was evaporated away under reduced pressure. The resulting residue was subjected to silica gel column chromatography, and the eluate with chloroform/methanol (10:1, v/v) gave the entitled compound (220 mg, 41.4%) as a white solid.

後処理

  1. temperatureAfter cooling
  2. concentrationconcentration under reduced pressure, dilution with chloroform
  3. washwashing with water
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated away under reduced pressure

出典と根拠

ORDレコード
ord-5f161c11eac9456fa0d0a6424277fa53
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

反応ノート

読み込み中…