Morpholine → 8-Chloro-4-(3-{[3-(morpholin-4-ylcarbonyl)benzyl]oxy}phenyl)-3-phenylcinnoline

HRID 643329노트

반응식

HRID 643329 반응식
C[Al](C)C.[NH:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.C[O:12][C:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][O:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]3[C:37]4[C:32](=[C:33]([Cl:38])[CH:34]=[CH:35][CH:36]=4)[N:31]=[N:30][C:29]=3[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH:23]=2)[CH:15]=1>C1(C)C=CC=CC=1>[Cl:38][C:33]1[CH:34]=[CH:35][CH:36]=[C:37]2[C:32]=1[N:31]=[N:30][C:29]([C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)=[C:28]2[C:24]1[CH:25]=[CH:26][CH:27]=[C:22]([O:21][CH2:20][C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([C:13]([N:5]3[CH2:10][CH2:9][O:8][CH2:7][CH2:6]3)=[O:12])[CH:15]=2)[CH:23]=1

참가 물질

5

반응물 3

HCID 8083MorpholineHCID 16682925TrimethylaluminumHCID 685788903-[3-(8-Chloro-3-phenyl-cinnolin-4-yl)-phenoxymethyl]-benzoic acid methyl ester

생성물 1

HCID 118548288-Chloro-4-(3-{[3-(morpholin-4-ylcarbonyl)benzyl]oxy}phenyl)-3-phenylcinnoline

시약·촉매·용매 1

HCID 1140Toluene용매2회

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온도
60 °C

실험 절차

A solution of trimethylaluminum (2 M solution in dichloromethane, 0.5 M) was added to a solution of morpholine (0.1 g) in 5 mL of toluene at room temperature. After 30 minutes 3-[3-(8-chloro-3-phenyl-cinnolin-4-yl)-phenoxymethyl]-benzoic acid methyl ester (50 mg) in 2 mL of toluene was added and the solution was heated to 60° C. for 15 hours. The reaction mixture was cooled to room temperature, quenched with diluted HCl and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4), and concentrated in vacuo. The residue was purified by semi-preparative HPLC. MS (ES) m/z 536.2.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customquenched with diluted HCl
  3. extractionextracted with ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by semi-preparative HPLC

출처 및 근거

ORD 기록
ord-66ef48f8ae354f8c96e89b6d5357e27e
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700595B2

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