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

HRID 1711705Notes

Reaction equation

HRID 1711705 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-b35db18494ca4aa792bef0cbdfa7a557
Source dataset
uspto-grants-2010_09
Patent number
US07790756B2

Reaction notes

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