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Sodium Hydroxide → HCID 67271565, 화합물

HRID 1696475
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HRID 1696475 반응식
[NH:1]1[CH:5]=[C:4]([C:6]2[CH:7]=[C:8]([N:12]3[C:16](N)=[CH:15][C:14]([C:18]([CH3:21])([CH3:20])[CH3:19])=[N:13]3)[CH:9]=[CH:10][CH:11]=2)[CH:3]=[N:2]1.[OH-:22].[Na+].Cl[C:25]([O:27][C:28]([CH3:30])=[CH2:29])=[O:26]>CCOC(C)=O>[C:18]([C:14]1[CH:15]=[C:16]([C:25]([O:27][C:28]([CH3:30])=[CH2:29])=[O:26])[N:12]([C:8]2[CH:7]=[C:6]([C:4]3[CH:3]=[N:2][N:1]([C:25]([O:27][C:28]([CH3:30])=[CH2:29])=[O:22])[CH:5]=3)[CH:11]=[CH:10][CH:9]=2)[N:13]=1)([CH3:21])([CH3:20])[CH3:19]
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참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 93846Isopropenyl chloroformateHCID 67271616HCID 67271616, 화합물

생성물 1

HCID 67271565HCID 67271565, 화합물수율 120.1%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

1-(3-(1H-pyrazol-4-yl)phenyl)-3-t-butyl-1H-pyrazol-5-amine (160 mg, 0.57 mmol) in EtOAc (3 mL) was cooled to 0° C. and treated with 1M NaOH (0.85 mL, 0.85 mmol) and isopropenyl chloroformate (0.080 mL, 0.74 mmol). The reaction was allowed to warm to RT overnight. The organic layer was washed with saturated NaHCO3, brine, dried (Na2SO4) and was concentrated to a film, which was dissolved in Et2O (5 mL) and the solution was lowed to stand overnight. The resultant crystals were collected, washed with Et2O and dried in vacuo to provide prop-1-en-2-yl 4-(3-(3-t-butyl-5-((prop-1-en-2-yloxy)carbonyl)-1H-pyrazol-1-yl)phenyl)-1H-pyrazole-1-carboxylate (193 mg, 75% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.73 (brs, 1H), 8.96 (d, J=−0.7 Hz, 1H), 8.46 (d, J=0.7 Hz, 1H), 7.87 (t, J=1.7 Hz, 1H), 7.81 (dt, J=8.2, 1.3 Hz, 1H), 7.54 (t, J=7.9 Hz, 1H), 7.41 (brd, J=7.9 Hz, 1H), 6.34 (s, 1H), 5.02 (s, 2H), 4.66 (brs, 1H), 4.57 (brs, 1H), 2.06 (s, 3H), 1.76 (brs, 3H), 1.30 (s, 9H). MS (ESI) m/z: 450.2 (M+H+).

후처리

  1. washThe organic layer was washed with saturated NaHCO3, brine
  2. dry with materialdried (Na2SO4)
  3. concentrationwas concentrated to a film, which
  4. dissolutionwas dissolved in Et2O (5 mL)
  5. customThe resultant crystals were collected
  6. washwashed with Et2O
  7. customdried in vacuo

출처 및 근거

ORD 기록
ord-393aeeea6fcb49919e1abdecb356ae19
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08163756B2

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