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Dichloromethane → 1-{5-[5-(4-Isopropoxyphenoxy)-1,3,4-thiadiazol-2-yl]thien-2-yl}ethanamine

HRID 404892
ノート
印刷プレビュー

反応式

HRID 404892 の反応式
[CH:1]([O:4][C:5]1[CH:34]=[CH:33][C:8]([O:9][C:10]2[S:14][C:13]([C:15]3[S:19][C:18]([CH:20]([N:22]4C(=O)C5C(=CC=CC=5)C4=O)[CH3:21])=[CH:17][CH:16]=3)=[N:12][N:11]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].O.NN.C(Cl)Cl>C(Cl)Cl.C(O)C>[CH:1]([O:4][C:5]1[CH:34]=[CH:33][C:8]([O:9][C:10]2[S:14][C:13]([C:15]3[S:19][C:18]([CH:20]([NH2:22])[CH3:21])=[CH:17][CH:16]=3)=[N:12][N:11]=2)=[CH:7][CH:6]=1)([CH3:2])[CH3:3]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 24654Hydrazine hydrate (1:1)HCID 694368152-(1-{5-[5-(4-isopropoxyphenoxy)-1,3,4-thiadiazol-2-yl]thien-2-yl}ethyl)-1H-isoindole-1,3(2H)-dione

生成物 1

HCID 694355961-{5-[5-(4-Isopropoxyphenoxy)-1,3,4-thiadiazol-2-yl]thien-2-yl}ethanamine収率 90.3%

試薬・触媒・溶媒 1

HCID 21584144Dichloromethane ethanol
溶媒

反応条件

温度
25 °C

実験手順

A solution of Example 24F (0.48 g, 0.98 mmol) in CH2Cl2/ethanol (1:1, v/v, 12 mL) was treated with hydrazine hydrate (0.476 mL, 9.79 mmol). The reaction was stirred at 25° C. for 5 hours and was concentrated under reduced pressure on a rotary evaporator to provide a residual oil. The concentrate was treated with CH2Cl2 (15 mL) and a white suspension formed. The suspension was filtered and the filtrate was concentrated on a rotary evaporator to provide 0.32 g of a pale yellow oil. The concentrate was purified by flash chromatography on silica gel eluting with a solvent gradient from 98:1:1 to 97:2:1 CH2Cl2/CH3OH/NH4OH to provide 0.09 g (25%) of the title compound as a colorless oil. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.46 (d, J=3.68 Hz, 1H) 7.38 (d, J=9.19 Hz, 2H) 7.02 (d, J=9.19 Hz, 2H) 6.96 (dd, J=3.68, 0.74 Hz, 1H) 4.63 (heptet, J=5.88 Hz, 1H) 4.17-4.29 (m, 1H) 1.35 (d, J=6.62 Hz, 3H) 1.28 (d, J=5.88 Hz, 6H); MS (APCI) m/z 362 (M+H)+.

後処理

  1. concentrationwas concentrated under reduced pressure on a rotary evaporator
  2. customto provide a residual oil
  3. customa white suspension formed
  4. filtrationThe suspension was filtered
  5. concentrationthe filtrate was concentrated on a rotary evaporator

出典と根拠

ORDレコード
ord-2a0a2c6f911246849491eb4d788bc08d
出典データセット
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08748627B2

反応ノート

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