Triethylamine → HCID 68587759、化合物

HRID 17348ノート

反応式

HRID 17348 の反応式
[CH2:1]([O:8][CH2:9][C:10]1[O:11][C:12]2[C:13](=[C:15]([C:27]#[N:28])[C:16]([CH3:26])=[C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:18]=2F)[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:36][N:37]([CH3:43])[C@H:38]1[CH2:42][CH2:41][NH:40][CH2:39]1.C(OCC)(=O)C>CS(C)=O.O>[CH2:1]([O:8][CH2:9][C:10]1[O:11][C:12]2[C:13](=[C:15]([C:27]#[N:28])[C:16]([CH3:26])=[C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:18]=2[N:40]2[CH2:41][CH2:42][C@H:38]([N:37]([CH3:43])[CH3:36])[CH2:39]2)[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 685869132-[(Benzyloxy)methyl]-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

生成物 1

HCID 68587759HCID 68587759、化合物収率 52%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

2-[(Benzyloxy)methyl]-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-90) (70 mg, 0.19 mmol) was dissolved in dimethyl sulfoxide (1.4 ml), triethylamine (63 μl, 0.45 mmol) and (3S)-3-(dimethylamino)pyrrolidine (29 μl, 0.23 mmol) were added, followed by stirring at 90° C. for 4 hours under nitrogen atmosphere. After cooling to room temperature, ethyl acetate was added, followed by fractionation with water. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was evaporated away and the resulting residue was subjected to preparative, thin-layer silica gel column, chromatography, eluted with a mixed solvent of chloroform/methanol (10:1, v/v) to obtain the entitled compound (46 mg, 52%) as a yellow oily substance.

後処理

  1. temperatureAfter cooling to room temperature
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated away
  5. washeluted with a mixed solvent of chloroform/methanol (10:1

出典と根拠

ORDレコード
ord-c39f998010154943a06b7a90bc4ff72a
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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