Pyridine → 2,2,2-trichloroethyl 3-tert-butyl-1-(1-oxo-1,2,3,4-tetrahydroisoquinolin-7-yl)-1H-pyrazol-5-ylcarbamate

HRID 2042125Notes

Reaction equation

HRID 2042125 reaction equation
Cl.[NH2:2][C:3]1[N:7]([C:8]2[CH:17]=[C:16]3[C:11]([CH2:12][CH2:13][NH:14][C:15]3=[O:18])=[CH:10][CH:9]=2)[N:6]=[C:5]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:4]=1.N1C=CC=CC=1.Cl[C:30]([O:32][CH2:33][C:34]([Cl:37])([Cl:36])[Cl:35])=[O:31]>C(Cl)Cl>[C:19]([C:5]1[CH:4]=[C:3]([NH:2][C:30](=[O:31])[O:32][CH2:33][C:34]([Cl:37])([Cl:36])[Cl:35])[N:7]([C:8]2[CH:17]=[C:16]3[C:11]([CH2:12][CH2:13][NH:14][C:15]3=[O:18])=[CH:10][CH:9]=2)[N:6]=1)([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 1049Pyridine2×HCID 870632,2,2-Trichloroethyl chloroformate2×HCID 67252821HCID 67252821, compound

Product 1

HCID 672526352,2,2-trichloroethyl 3-tert-butyl-1-(1-oxo-1,2,3,4-tetrahydroisoquinolin-7-yl)-1H-pyrazol-5-ylcarbamateYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 7-(5-amino-3-t-butyl-pyrazol-1-yl)-3,4-dihydro-2H-isoquinolin-1-one hydrochloride (0.5 g, 1.76 mmol) in CH2Cl2 (25 mL) were added pyridine (0.22 mL) and trichloroethyl chloroformate (0.27 mL) at 0° C. and the mixture was stirred overnight at RT. LCMS showed the reaction was incomplete. Pyridine (0.25 mL) and TROC-Cl (0.25 mL) were added and then the mixture stirred at RT for 2 hours. The reaction mixture was diluted with CH2Cl2, the organic layer was washed with 3M HCl and brine, dried (Na2SO4) and concentrated in vacuo. The residue was dissolved in EtOAc and hexane was added. The solid was filtered to obtain 2,2,2-trichloroethyl 3-tert-butyl-1-(1-oxo-1,2,3,4-tetrahydroisoquinolin-7-yl)-1H-pyrazol-5-ylcarbamate (0.46 g, 57% yield). MS (ESI) m/z: 458.0 (M+H+).

Workup

  1. stirringthe mixture stirred at RT for 2 hours
  2. washthe organic layer was washed with 3M HCl and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in EtOAc
  6. additionhexane was added
  7. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-1bb241f1ee5142e2a72f5ef76dacad79
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

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