Diisopropylethylamine → N-(4-chlorobenzyl)-2-{[(2-hydroxy-3-phenylpropyl)(methyl)amino]methyl}-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

HRID 23670ノート

反応式

HRID 23670 の反応式
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:23])[C:12]3[S:19][C:18]([CH2:20]Cl)=[C:17]([CH3:22])[C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1.[CH3:26][NH:27][CH2:28][CH:29]([OH:37])[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:23])[C:12]3[S:19][C:18]([CH2:20][N:27]([CH2:28][CH:29]([OH:37])[CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH3:26])=[C:17]([CH3:22])[C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 30471961-(Methylamino)-3-phenylpropan-2-olHCID 22574363N-(4-chlorobenzyl)-2-(chloromethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

生成物 1

HCID 22574398N-(4-chlorobenzyl)-2-{[(2-hydroxy-3-phenylpropyl)(methyl)amino]methyl}-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide収率 71.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of N-(4-chlorobenzyl)-2-(chloromethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide (100 mg, 0.25 mmol), 1-(methylamino)-3-phenylpropan-2-ol (Eur. J Med. Chem.—Chim. Ther. 1979, 14, 165-70)(63 mg, 0.38 mmol) and diisopropylethylamine (67 μL, 0.38 mmol) in dry DMF (5.0 mL) was stirred for 24 hours at room temperature. The solution was diluted with water (15 mL). The resulting milky suspension was stirred vigorously for 30 minutes, and then left standing overnight at room temp. The mixture was filtered, and the collected solid was washed with water and dried in vacuo, leaving a white solid. Recrystallization from acetonitrile (10 mL, dissolved with warming and then cooled to 0° C. overnight) gave the title compound (94 mg) as a white solid.

後処理

  1. stirringThe resulting milky suspension was stirred vigorously for 30 minutes
  2. waitleft
  3. waitstanding overnight at room temp
  4. filtrationThe mixture was filtered
  5. washthe collected solid was washed with water
  6. customdried in vacuo
  7. customleaving a white solid
  8. customRecrystallization from acetonitrile (10 mL
  9. dissolutiondissolved
  10. temperaturewith warming
  11. temperaturecooled to 0° C. overnight)

出典と根拠

ORDレコード
ord-520da8ff56e44e56a34e1170c974625a
出典データセット
uspto-grants-2005_02
特許番号
US06852731B2

反応ノート

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