Diisopropylethylamine → HCID 10391154、化合物

HRID 982722

反応式

HRID 982722 の反応式
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:22])[C:12]3[S:19][C:18]([CH2:20]Cl)=[CH:17][C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1.[CH3:25][NH:26][CH2:27][C@H:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=1)[OH:29].C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:22])[C:12]3[S:19][C:18]([CH2:20][N:26]([CH2:27][C@@H:28]([OH:29])[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=4)[CH3:25])=[CH:17][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 10149007(R)-2-(methylamino)-1-pyridin-2-ylethanolHCID 22563229N-(4-chlorobenzyl)-2-(chloromethyl)-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

生成物 1

HCID 10391154HCID 10391154、化合物収率 65.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

A mixture of N-(4-chlorobenzyl)-2-(chloromethyl)-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide (113 mg, 0.30 mmol), (1R)-2-(methylamino)-1-pyridin-2-ylethanol (Preparation 28) (100 mg, 0.44 mmol) and diisopropylethylamine (230 μL, 1.32 mmol) in dry DMF (8 mL) was heated to 60° C., becoming a solution. The reaction was stirred for 7 hours at that temperature. After cooling to room temperature, the solution was diluted with water (12 mL). The resulting milky suspension was stirred vigorously for 30 minutes, and then left standing overnight in the refrigerator. The mixture was filtered, and the collected solid was washed with water and dried in vacuo, leaving a white solid. Recrystallization from acetonitrile/water (dissolved with warming 5 mL of acetonitrile, then cooled to 0° C. and then diluted with 1 mL of water, left overnight) gave the title compound (98 mg) as a white solid.

後処理

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

出典と根拠

ORDレコード
ord-34a0ac25195f4337a17fd9b389e71dde
出典データセット
uspto-grants-2005_03
特許番号
US06861438B2

関連ノート

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