4-(4-Fluorophenyl)-2-oxo-2H-chromene-7-carbaldehyde → 7-({[5-(1-Ethyl-1-hydroxypropyl)-1,3,4-oxadiazol-2-yl]amino}methyl)-4-(4-fluorophenyl)-2H-chromen-2-one

HRID 1988201ノート

反応式

HRID 1988201 の反応式
[NH2:1][C:2]1[O:6][C:5]([C:7]([OH:12])([CH2:10][CH3:11])[CH2:8][CH3:9])=[N:4][N:3]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:29]3[C:24](=[CH:25][C:26]([CH:30]=O)=[CH:27][CH:28]=3)[O:23][C:22](=[O:32])[CH:21]=2)=[CH:16][CH:15]=1>C1(C)C=CC=CC=1>[CH2:8]([C:7]([C:5]1[O:6][C:2]([NH:1][CH2:30][C:26]2[CH:25]=[C:24]3[C:29]([C:20]([C:17]4[CH:18]=[CH:19][C:14]([F:13])=[CH:15][CH:16]=4)=[CH:21][C:22](=[O:32])[O:23]3)=[CH:28][CH:27]=2)=[N:3][N:4]=1)([OH:12])[CH2:10][CH3:11])[CH3:9]

参加物

4

反応物 2

HCID 468452294-(4-Fluorophenyl)-2-oxo-2H-chromene-7-carbaldehydeHCID 574378393-(5-Amino-1,3,4-oxadiazol-2-yl)pentan-3-ol

生成物 1

HCID 118569667-({[5-(1-Ethyl-1-hydroxypropyl)-1,3,4-oxadiazol-2-yl]amino}methyl)-4-(4-fluorophenyl)-2H-chromen-2-one

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A mixture of 3-(5-amino-1,3,4-oxadiazol-2-yl)pentan-3-ol (0.446 g, 2.6 mmol) and 4-(4-fluorophenyl)-2-oxo-2H-chromene-7-carbaldehyde (0.350 g, 1.3 mmol) in 5 mL of toluene was refluxed with a Dean-Stark trap overnight. After cooling to rt the solvent was removed and the crude imine diluted in ethanol (8 ml) at 0° C. Solid NaBH4 (49 mg) was added to the solution and after 30 min of stirring aqueous NH4Cl was added to destroy the excess hydride. After dilution with EtOAc-brine, the organic phase was dried with MgSO4. Purification on silica gel with toluene-EtOAc (2:8) gave the title compound. 1H NMR (400 MHz, acetone-d6): δ 7.67 (m, 2H), 7.48 (m, 2H), 7.37 (m, 3H), 7.19 (bt, 1H), 6.33 (s, 1H), 4.66 (m, 2H), 4.31 (s, 1H), 1.85 (m, 4H), 0.85 (t, 6H).

後処理

  1. temperaturewas refluxed with a Dean-Stark trap overnight
  2. customwas removed
  3. additionthe crude imine diluted in ethanol (8 ml) at 0° C
  4. additionSolid NaBH4 (49 mg) was added to the solution and after 30 min of stirring aqueous NH4Cl
  5. additionwas added
  6. customto destroy the excess hydride
  7. dry with materialAfter dilution with EtOAc-brine, the organic phase was dried with MgSO4
  8. customPurification on silica gel with toluene-EtOAc (2:8)

出典と根拠

ORDレコード
ord-79e7da6926b14597b1a271973d1660a7
出典データセット
uspto-grants-2009_06
特許番号
US07553973B2

反応ノート

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