Sodium Hydroxide → HCID 67271565, compound

HRID 1696475Notes

Reaction equation

HRID 1696475 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 67271565HCID 67271565, compoundYield 120.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-393aeeea6fcb49919e1abdecb356ae19
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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