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Pyridine → (5-tert-Butyl-2-{3-[(2-dimethylamino-ethyl)-methyl-amino]-phenyl}-2H-pyrazol-3-yl)-carbamic acid phenyl ester

HRID 630960
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인쇄 미리보기

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HRID 630960 반응식
[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([N:13]([CH3:19])[CH2:14][CH2:15][N:16]([CH3:18])[CH3:17])[CH:10]=[CH:11][CH:12]=2)[N:5]=[C:4]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:3]=1.N1C=CC=CC=1.Cl[C:31]([O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:32]>C(Cl)Cl.O>[C:34]1([O:33][C:31](=[O:32])[NH:1][C:2]2[N:6]([C:7]3[CH:12]=[CH:11][CH:10]=[C:9]([N:13]([CH2:14][CH2:15][N:16]([CH3:18])[CH3:17])[CH3:19])[CH:8]=3)[N:5]=[C:4]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:3]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1
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참가 물질

6

반응물 3

HCID 1049Pyridine2회HCID 15891Phenyl chloroformate2회HCID 89612440HCID 89612440, 화합물

생성물 1

HCID 86687275(5-tert-Butyl-2-{3-[(2-dimethylamino-ethyl)-methyl-amino]-phenyl}-2H-pyrazol-3-yl)-carbamic acid phenyl ester수율 43%

시약·촉매·용매 2

HCID 962Water용매
HCID 6344
Dichloromethane
용매

실험 절차

A solution of Intermediate 150b (50 mg, 0.16 mmol) in DCM (2 mL) was treated with pyridine (26 μL, 0.32 mmol) and phenyl chloroformate (32 μL, 0.25 mmol). The resulting mixture was stirred at RT for 2 h. Further pyridine (26 μL, 0.32 mmol) and phenyl chloroformate (32 μL, 0.25 mmol) were added and the mixture stirred at RT for 16 h. The mixture was diluted with water and the phases separated. The aqueous layer was extracted with DCM and the combined organic phase was washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was purified by FCC, using 0-20% MeOH in DCM, to give the title compound (30 mg, 43%). LCMS (Method 3): Rt 2.97 min, m/z 436 [MH+].

후처리

  1. stirringthe mixture stirred at RT for 16 h
  2. customthe phases separated
  3. extractionThe aqueous layer was extracted with DCM
  4. washthe combined organic phase was washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by FCC

출처 및 근거

ORD 기록
ord-a67d246ad31f4a3ea12c0a1b11e77a9d
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09315503B2

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