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Diisopropylethylamine → 3-methoxy-N-[(3R)-1-methylpyrrolidin-3-yl]-4-nitro-benzamide

HRID 2234458
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HRID 2234458 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:6](Cl)=[O:7].C(N(CC)C(C)C)(C)C.Cl.Cl.[CH3:26][N:27]1[CH2:31][CH2:30][C@@H:29]([NH2:32])[CH2:28]1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:6]([NH:32][C@@H:29]1[CH2:30][CH2:31][N:27]([CH3:26])[CH2:28]1)=[O:7]
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참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 111276553-methoxy-4-nitro-benzoyl Chloride2회HCID 53256048(3R)-1-Methyl-3-PyrrolidinaMine hydrochloride2회

생성물 1

HCID 686830363-methoxy-N-[(3R)-1-methylpyrrolidin-3-yl]-4-nitro-benzamide수율 47%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

3-methoxy-4-nitro-benzoyl chloride (Intermediate 189; 374 mg, 1.73 mmol) was dissolved in DCM (20 mL) and N,N-diisopropylethylamine (0.96 mL, 5.54 mmol) added. The mixture was cooled in an ice/water bath and (3R)-1-methylpyrrolidin-3-amine dihydrochloride (Intermediate 184; 300 mg, 1.73 mmol) in DCM (10 mL) added dropwise. The mixture was allowed to warm to room temperature and stirred for 0.5 hour. The mixture was washed with brine, 2N NaOH(aq), dried with MgSO4 and evaporated to yield the title compound as a brown solid (227 mg, 46.9%).

후처리

  1. temperatureThe mixture was cooled in an ice/water bath
  2. washThe mixture was washed with brine, 2N NaOH(aq)
  3. dry with materialdried with MgSO4
  4. customevaporated

출처 및 근거

ORD 기록
ord-ceb02e1255be4dd89cc2316532daad46
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07709471B2

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