Diisopropylethylamine → HCID 178458665、化合物

HRID 75897ノート

反応式

HRID 75897 の反応式
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([O:14][CH:15]([CH3:17])[CH3:16])[NH:11][N:10]=2)[C:5]([N+:18]([O-:20])=[O:19])=[CH:4][CH:3]=1.[NH2:21][C@H:22]([C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)[CH2:23][OH:24].CCN(C(C)C)C(C)C>CCCCO>[F:31][C:28]1[CH:27]=[CH:26][C:25]([C@@H:22]([NH:21][C:2]2[CH:3]=[CH:4][C:5]([N+:18]([O-:20])=[O:19])=[C:6]([NH:8][C:9]3[CH:13]=[C:12]([O:14][CH:15]([CH3:17])[CH3:16])[NH:11][N:10]=3)[N:7]=2)[CH2:23][OH:24])=[CH:30][CH:29]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 10583003(R)-2-Amino-2-(4-fluorophenyl)ethanolHCID 178458609HCID 178458609、化合物

生成物 1

HCID 178458665HCID 178458665、化合物収率 87%

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

反応条件

温度
165 °C

実験手順

A mixture of 6-chloro-N-(5-isopropoxy-1H-pyrazol-3-yl)-3-nitropyridin-2-amine (Method 28; 0.25 g, 0.84 mmol), (R)-2-amino-2-(4-fluorophenyl)ethanol (0.15 g, 0.97 mmol) and DIEA (0.16 ml, 0.92 mmol) in n-BuOH (3 ml) was heated in a sealed tube at 165° C. for 4 hours. The solvent was removed under reduced pressure and the residue was purified by column chromatography (hexane-EtOAc=1:2) to give the title compound as a yellow solid (0.30 g, 87%). 1H NMR (400 MHz) δ 12.12, 12.10 & 11.61 (s, 1H), 10.94, 10.89 & 10.74 (s, 1H), 9.05, 8.82 & 8.73 (d, J=7.2 Hz, 1H), 8.13 & 8.11 (d, J=9.2 Hz, 1H), 7.45-7.32 (m, 2H), 7.20-7.10 (m, 2H), 6.32 & 6.07 (d, J=9.2 Hz, 1H), 5.90, 5.83 & 5.79 (s, 1H), 5.23, 5.12 & 4.78 (m, 2H), 4.71, 4.64 & 4.37 (m, 1H), 3.69 (m. 2H), 1.34 & 1.29 (d, J=6.0 Hz, 6H). MS: Calcd.: 416. Found: [M+H]+ 417.

後処理

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by column chromatography (hexane-EtOAc=1:2)

出典と根拠

ORDレコード
ord-e2950402975940fd9b0ee126a65dbade
出典データセット
uspto-grants-2014_09
特許番号
US08835465B2

反応ノート

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