Hydrochloric Acid → HCID 178439655、化合物

HRID 2267001

反応式

HRID 2267001 の反応式
[C:1]([C:4]1[CH:26]=[CH:25][C:7]([O:8][CH2:9][C:10]2[CH:11]=[C:12]([CH:22]=[CH:23][CH:24]=2)[O:13][C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][N:15]=2)=[C:6]([CH2:27][CH2:28][CH3:29])[C:5]=1[OH:30])(=[O:3])[CH3:2].C(O)(C)C.[N-:35]=[N+:36]=[N-:37].[Na+].Cl>[Br-].[Zn+2].[Br-].O>[OH:30][C:5]1[C:6]([CH2:27][CH2:28][CH3:29])=[C:7]([O:8][CH2:9][C:10]2[CH:24]=[CH:23][CH:22]=[C:12]([O:13][C:14]3[CH:21]=[CH:20][C:17]([C:18]4[NH:37][N:36]=[N:35][N:19]=4)=[CH:16][N:15]=3)[CH:11]=2)[CH:25]=[CH:26][C:4]=1[C:1](=[O:3])[CH3:2]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 33557Sodium AzideHCID 685352096-[3-(4-Acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenoxy]-nicotinonitrile

生成物 1

HCID 178439655HCID 178439655、化合物収率 68%

試薬・触媒・溶媒 2

HCID 10421208Zinc bromide触媒HCID 962Water溶媒

反応条件

温度
130 °C

実験手順

Mix 6-[3-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenoxy]-nicotinonitrile of Preparation 42, (0.33 g, 0.83 mmol), isopropyl alcohol (5 mL), zinc bromide (1.12 g, 4.98 mmol), sodium azide (0.32 g, 4.98 mmol) and water (5 mL) in a pressure flask. Seal the flask and heat to 130° C. in an oil bath for 6 hr. Allow to cool to ambient temperature and pour into 1N hydrochloric acid (50 mL). Filter the white solid and purify by flash chromatography, using 40:1 chloroformchloroform/methanol+1% acetic acid to 20:1 chloroformchloroform/methanol+1% acetic acid as a gradient eluent to give the title compound (0.25 g, 68%): MS (m/z): 444.2 (M−1). 1H NMR (DMSO-d6) 12.86 (s, 1H), 8.80 (s, 1H), 8.46 (d, J=8.2 Hz, 1H), 7.84 (d, J=8.8 Hz, 1H), 7.52 (t, J=8.2 Hz, 1H), 7.37-7.28 (m, 3H), 7.20 (d, J=8.2 Hz, 1H), 6.75 (d, J=8.8 Hz, 1H), 5.32 (s, 2H), 2.63-2.55 (m, 5H), 1.51-1.41 (m, 2H), 0.82 (t, J=7.2 Hz, 3H).

後処理

  1. additionMix
  2. customSeal the flask
  3. temperatureto cool to ambient temperature
  4. filtrationFilter the white solid
  5. custompurify by flash chromatography

出典と根拠

ORDレコード
ord-16acd490693c43328211ae966fbc078a
出典データセット
uspto-grants-2010_12
特許番号
US07858646B2

関連ノート

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