Dichloromethane → HCID 69192623、化合物

HRID 1020273ノート

反応式

HRID 1020273 の反応式
[H-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][OH:7].[F:8][C:9]1[CH:10]=[C:11]([CH:24]=[CH:25][CH:26]=1)[CH2:12][NH:13][C:14]([NH:16][C:17]1[S:21][N:20]=[C:19]([CH2:22]Cl)[N:18]=1)=[O:15].ClCCl>C1COCC1>[F:8][C:9]1[CH:10]=[C:11]([CH:24]=[CH:25][CH:26]=1)[CH2:12][NH:13][C:14]([NH:16][C:17]1[S:21][N:20]=[C:19]([CH2:22][O:7][CH2:6][CH2:5][O:4][CH3:3])[N:18]=1)=[O:15]

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 58055089HCID 58055089、化合物2 回

生成物 1

HCID 69192623HCID 69192623、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Sodium hydride (4 eq, 2.66 mmol, 0.13 g of a 50 wt-% suspension in oil) was suspended in THF (2 mL) and cooled to 0° C. 2-methoxy ethanol (3 eq, 1.99 mmol, 0.15 g) and 15-crown-5-ether (1 drop) were added. 1-(3-Fluorobenzyl)-3-(3-(chloromethyl)-1,2,4-thiadiazol-5-yl)urea (Intermediate XXV) was added and the mixture was stirred over night with temperature allowed to rise to room temperature. Dichloromethane (50 mL) was added. The mixture was washed with water (2×10 mL), dried (Na2SO4), filtered and concentrated in vacuo. The crude material (0.2 g of an oil) was further purified by preparative HPLC to give 0.101 g. 1H-NMR (300 MHz, CD3OD): δ 7.34 (m, 1H), 7.14 (d, 1H), 7.07 (d, 1H), 6.99 (m, 1H), 4.58 (s, 2H), 4.45 (s, 2H), 3.70 (t, 2H), 3.56 (t, 2H), 3.30 (s, 3H).

後処理

  1. customto rise to room temperature
  2. washThe mixture was washed with water (2×10 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material (0.2 g of an oil) was further purified by preparative HPLC
  7. customto give 0.101 g

出典と根拠

ORDレコード
ord-f5f8a67c92dd4b9f9370aa846e916fce
出典データセット
uspto-grants-2014_05
特許番号
US08716320B2

反応ノート

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