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Potassium Carbonate → 2-(6-Bromophthalazin-1-yl)-5-isopropyl-2,5-diaza-bicyclo[2.2.1]heptane

HRID 2357575
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HRID 2357575 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](Cl)=[N:7][N:6]=[CH:5]2.Cl.Cl.[CH:15]([N:18]1[CH2:23][CH:22]2[CH2:24][CH:19]1[CH2:20][NH:21]2)([CH3:17])[CH3:16].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N:21]1[CH2:20][CH:19]3[CH2:24][CH:22]1[CH2:23][N:18]3[CH:15]([CH3:17])[CH3:16])=[N:7][N:6]=[CH:5]2
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 220304246-Bromo-1-chlorophthalazineHCID 684560752-Isopropyl-2,5-diazabicyclo[2.2.1]heptane dihydrochloride

생성물 1

HCID 684549782-(6-Bromophthalazin-1-yl)-5-isopropyl-2,5-diaza-bicyclo[2.2.1]heptane수율 46.7%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
130 °C

실험 절차

A mixture of 6-bromo-1-chlorophthalazine (Example 1, 90 mg, 370 μmol), 2-isopropyl-2,5-diaza-bicyclo[2.2.1]heptane dihydrochloride (95 mg, 444 μmol) and potassium carbonate (153 mg, 1109 μmol) in 10 mL acetonitrile was stirred at 130° C. under in a sealed tube. The mixture turned red in about 5 min. The reaction was monitored by MS. After about 1 h at 130° C., MS and TLC showed all starting material was converted to product (M+1=347, 349). The mixture was cooled down to room temperature, and concentrated on a Rotavaporator. After purification by column (eluting with gradient of 2-10% 2M ammonia in methanol to DCM), 2-(6-bromophthalazin-1-yl)-5-isopropyl-2,5-diaza-bicyclo[2.2.1]heptane (60 mg) was obtained as a yellow solid.

후처리

  1. waitAfter about 1 h at 130° C.
  2. temperatureThe mixture was cooled down to room temperature
  3. concentrationconcentrated on a Rotavaporator
  4. customAfter purification
  5. washby column (eluting with gradient of 2-10% 2M ammonia in methanol to DCM)

출처 및 근거

ORD 기록
ord-fd80c4107ed34b238a174c7c744eabdc
출처 데이터셋
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07759337B2

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