Sodium Iodide → 7-(4-(4-(2-isopropoxyphenyl)-1,4-diazepan-1-yl)butoxy)quinolin-2(1H)-one

HRID 1750107ノート

反応式

HRID 1750107 の反応式
ClC1C(Cl)=CC=CC=1N1CCCN([CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:29]=[C:28]3[C:23]([CH:24]=[CH:25][C:26](=[O:30])[NH:27]3)=[CH:22][CH:21]=2)CC1.[Na+].[I-].Cl.[CH:34]([O:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[N:44]1[CH2:50][CH2:49][CH2:48][NH:47][CH2:46][CH2:45]1)([CH3:36])[CH3:35].[C:51]([O-])([O-])=O.[K+].[K+]>CC#N.O>[CH:34]([O:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[N:44]1[CH2:50][CH2:49][CH2:48][N:47]([CH2:51][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:29]=[C:28]3[C:23]([CH:24]=[CH:25][C:26](=[O:30])[NH:27]3)=[CH:22][CH:21]=2)[CH2:46][CH2:45]1)([CH3:36])[CH3:35]

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 565980747-(3-(4-(2,3-dichlorophenyl)-1,4-diazepan-1-yl)propoxy)quinolin-2(1H)-oneHCID 666318431-(2-Isopropoxyphenyl)-1,4-diazepane hydrochloride

生成物 1

HCID 565990117-(4-(4-(2-isopropoxyphenyl)-1,4-diazepan-1-yl)butoxy)quinolin-2(1H)-one収率 62.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

A mixture of intermediate 15 (120 mg, 0.41 mmol) and NaI (123 mg, 0.82 mmol) in CH3CN was heated to reflux for 30 min and then cooled to rt. Intermediate 34 (111 mg, 0.41 mmol) and anhydrous K2CO3 (226 mg, 1.64 mmol) were added to the mixture. The resulting mixture was heated to reflux and stirred overnight. The reaction solution was diluted with water and extracted with EtOAc. The combined EtOAc layers were washed with brine, dried over anhydrous Na2SO4, concentrated in vacuo and purified by flash chromatography on silica gel column (elution with DCM/MeOH=50:1) to give 7-(4-(4-(2-isopropoxyphenyl)-1,4-diazepan-1-yl)butoxy)quinolin-2(1H)-one (compound 18) (115 mg, 62%). 1H NMR (300 MHz, CDCl3) δ 11.68 (bs., 1H), 7.71 (d, J=9.3 Hz, 1H), 7.44 (d, J=9.3 Hz, 1H), 6.89-6.79 (m, 6H), 6.53 (d, J=9.6 Hz, 1H), 4.62-4.54 (m, 1H), 4.11-4.07 (m, 2H), 3.34-3.29 (m, 4H), 2.94-2.86 (m, 4H), 2.72-2.62 (m, 2H), 2.12-1.96 (m, 2H), 1.87-1.76 (m, 4H), 1.35 (d, J=6.0 Hz, 6H). HPLC: 99%, RT 2.434 min. MS (ESI) m/z 450.3 [M+H]+.

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 30 min
  3. temperatureThe resulting mixture was heated
  4. temperatureto reflux
  5. extractionextracted with EtOAc
  6. washThe combined EtOAc layers were washed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated in vacuo
  9. custompurified by flash chromatography on silica gel column (elution with DCM/MeOH=50:1)

出典と根拠

ORDレコード
ord-95d1d64a130747b7856b879c390c3564
出典データセット
uspto-grants-2015_10
特許番号
US09156822B2

反応ノート

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