4-Methylmorpholine → HCID 178431437、化合物

HRID 2362808

反応式

HRID 2362808 の反応式
[CH3:1][C:2]1([CH3:21])[O:6][CH:5]([CH2:7][O:8][C:9]2[CH:20]=[CH:19][C:12]([CH:13]=[C:14]([C:17]#[N:18])[C:15]#[N:16])=[CH:11][CH:10]=2)[CH2:4][O:3]1.[C:22]([CH2:24][C:25]([NH2:27])=[S:26])#[N:23].CN1CCOCC1>C(O)C>[NH2:18][C:17]1[C:14]([C:15]#[N:16])=[C:13]([C:12]2[CH:11]=[CH:10][C:9]([O:8][CH2:7][CH:5]3[CH2:4][O:3][C:2]([CH3:21])([CH3:1])[O:6]3)=[CH:20][CH:19]=2)[C:24]([C:22]#[N:23])=[C:25]([SH:26])[N:27]=1

参加物

5

反応物 3

HCID 79724-MethylmorpholineHCID 14162772-CyanoethanethioamideHCID 59201939{4-[(2,2-Dimethyl-1,3-dioxolan-4-yl)methoxy]benzylidene}malononitrile

生成物 1

HCID 178431437HCID 178431437、化合物

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

0.43 g (1.51 mmol) of the compound from Example 2A, 0.38 g (3.78 mmol) of cyanothioacetamide and 0.38 g (3.78 mmol) of 4-methylmorpholine are dissolved in 15 ml of ethanol, and the mixture is stirred under reflux for 6 h. After cooling, the reaction solution is concentrated using a rotary evaporator, and the residue is chromatographed on silica gel 60. After removal of by-products (mobile phase gradient cyclohexane→cyclohexane/ethyl acetate 1:1), the product fractions are eluted (mobile phase gradient ethyl acetate→ethyl acetate/methanol 20:1). This is followed by fine purification via preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5).

後処理

  1. temperatureunder reflux for 6 h
  2. temperatureAfter cooling
  3. concentrationthe reaction solution is concentrated
  4. customa rotary evaporator
  5. customthe residue is chromatographed on silica gel 60
  6. customAfter removal of by-products (mobile phase gradient cyclohexane→cyclohexane/ethyl acetate 1:1)
  7. washthe product fractions are eluted (mobile phase gradient ethyl acetate→ethyl acetate/methanol 20:1)
  8. customThis is followed by fine purification via preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)

出典と根拠

ORDレコード
ord-83e771eaf1d441f284fecc051225ddc6
出典データセット
uspto-grants-2014_04
特許番号
US08691850B2

関連ノート

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