N,N-Dimethylaniline → 10-(9H-Fluoren-2-ylcarbonyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine

HRID 2244297

반응식

HRID 2244297 반응식
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[NH:7][CH2:6][C:5]=12.[CH:15]1[C:27]2[CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]=2[CH:18]=[CH:17][C:16]=1[C:28](Cl)=[O:29].C1C2CC3C(=CC=CC=3)C=2C=CC=1C(O)=O.S(Cl)(Cl)=O.CN(C)C1C=CC=CC=1>O1CCOCC1.O>[CH:15]1[C:27]2[CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]=2[CH:18]=[CH:17][C:16]=1[C:28]([N:7]1[C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[CH2:10][N:4]2[CH:3]=[CH:2][CH:1]=[C:5]2[CH2:6]1)=[O:29]

참가 물질

8

반응물 5

HCID 949N,N-DimethylanilineHCID 24386Thionyl ChlorideHCID 3485919H-fluorene-2-carboxylic acidHCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepineHCID 178156299H-Fluorene-2-carbonyl chloride

생성물 1

HCID 6869069310-(9H-Fluoren-2-ylcarbonyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine수율 95.4%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

A solution containing 1.84 g (0.01 mol) of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine, 2.28 g (0.01 mol) of 9H-fluorene-2-carbonyl chloride (generated via the reaction of 9H-fluorene-2-carboxylic acid and thionyl chloride) and 1.21 g (0.01 mol) of N,N-dimethylaniline in 125 mL of 1,4-dioxane was allowed to stand at room temperature for two hours. The reaction mixture was poured into 1 L of water, the precipitate was collected, washed with water and dried to provide the title compound (3.59 g). The material was recrystallized from acetone, m.p. 202-204° C.

후처리

  1. customthe precipitate was collected
  2. washwashed with water
  3. customdried

출처 및 근거

ORD 기록
ord-609afa89bb224a938f4c0c410a614c1e
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07678787B2

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