Diisopropylethylamine → 7-[3-[(7-Methoxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)amino]propoxy]chromen-4-one

HRID 5572

反応式

HRID 5572 の反応式
Cl.[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][CH:10]([CH2:13][NH2:14])[O:9][C:8]=2[CH:15]=1.Br[CH2:17][CH2:18][CH2:19][O:20][C:21]1[CH:30]=[C:29]2[C:24]([C:25](=[O:31])[CH:26]=[CH:27][O:28]2)=[CH:23][CH:22]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][CH:10]([CH2:13][NH:14][CH2:17][CH2:18][CH2:19][O:20][C:21]3[CH:30]=[C:29]4[C:24]([C:25](=[O:31])[CH:26]=[CH:27][O:28]4)=[CH:23][CH:22]=3)[O:9][C:8]=2[CH:15]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 189238737-Methoxy-2,3-dihydro-1,4-benzodioxin-2-methanamine hydrochlorideHCID 197967547-(3-Bromopropoxy)chromen-4-one

生成物 1

HCID 197967537-[3-[(7-Methoxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)amino]propoxy]chromen-4-one収率 4.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

2,3-Dihydro-7-methoxy-1,4-benzodioxin-2-methanamine hydrochloride (4.0 g, 17 mmole), 7-(3-bromopropoxy)chromen-4-one (4.9 g, 17 mmole) and diisopropylethylamine (15.1 ml, 87 mmole) were combined in 150 ml of DMF and heated at 80° C. for 24 hours under a nitrogen atmosphere. The solvent was then removed and replaced with dichloromethane. The mixture was washed with an equal volume of saturated aqueous sodium bicarbonate, with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuum. The residue was chromatographed on a silica gel column using first dichloromethane and then 5% methanolic dichloromethane as eluents. The fractions containing material with Rf=0.59 on silica gel tlc (chloroform/methanol/ammonia=95/5/1) were combined, concentrated, and the residue was dissolved in 50% methanol/dichloromethane. The mixture was then treated with 4N isopropanolic HCl until the solution was 3 in pH and crystallized by triturating with ether. Two further recrystallizations gave 0.3 g of title compound as a yellow solid hydrochloride, quarter hydrate, m.p. 155°-157° C.

後処理

  1. customThe solvent was then removed
  2. washThe mixture was washed with an equal volume of saturated aqueous sodium bicarbonate, with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum
  6. customThe residue was chromatographed on a silica gel column
  7. additionThe fractions containing material with Rf=0.59 on silica gel tlc (chloroform/methanol/ammonia=95/5/1)
  8. concentrationconcentrated
  9. dissolutionthe residue was dissolved in 50% methanol/dichloromethane
  10. additionThe mixture was then treated with 4N isopropanolic HCl until the solution
  11. customcrystallized
  12. customby triturating with ether
  13. customTwo further recrystallizations

出典と根拠

ORDレコード
ord-5865d24af6cd479aaec4ce67db420a22
出典データセット
uspto-grants-1993_09
特許番号
US05245051

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