Triethylamine → Carbonic acid ethyl ester 3-methoxy-9-oxo-8-(2,4,6-trimethyl-phenyl)-2,3,4,5-tetrahydro-1H,9H-pyrazolo[1,2-a][1,2,5]triazepin-7-yl ester

HRID 924603Notes

Reaction equation

HRID 924603 reaction equation
[CH3:1][O:2][N:3]1[CH2:9][CH2:8][N:7]2[C:10](=[O:23])[CH:11]([C:14]3[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=3[CH3:22])[C:12](=[O:13])[N:6]2[CH2:5][CH2:4]1.C(N(CC)CC)C.Cl[C:32]([O:34][CH2:35][CH3:36])=[O:33]>CN(C)C1C=CN=CC=1.O1CCCC1>[CH3:1][O:2][N:3]1[CH2:4][CH2:5][N:6]2[C:12](=[O:13])[C:11]([C:14]3[C:15]([CH3:22])=[CH:16][C:17]([CH3:21])=[CH:18][C:19]=3[CH3:20])=[C:10]([O:23][C:32](=[O:33])[O:34][CH2:35][CH3:36])[N:7]2[CH2:8][CH2:9]1

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 10928Ethyl chloroformate2×HCID 867199153-Methoxy-8-(2,4,6-trimethyl-phenyl)-tetrahydro-pyrazolo[1,2-a][1,2,5]triazepine-7,9-dione

Product 1

HCID 71479406Carbonic acid ethyl ester 3-methoxy-9-oxo-8-(2,4,6-trimethyl-phenyl)-2,3,4,5-tetrahydro-1H,9H-pyrazolo[1,2-a][1,2,5]triazepin-7-yl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-methoxy-8-(2,4,6-trimethyl-phenyl)-tetrahydro-pyrazolo[1,2-a][1,2,5]triazepine-7,9-dione (106 mg, 0.33 mmol), triethylamine (0.070 ml, 51 mg, 0.50 mmol) and a catalytic amount of 4-dimethylaminopyridine in tetrahydrofuran (2 ml) at 0° C. was added ethyl chloroformate (0.035 ml, 40 mg, 0.37 mmol) dropwise. The suspension was stirred at 0° C. for 20 minutes, treated with more triethylamine (0.070 ml, 51 mg, 0.50 mmol) and ethyl chloroformate (0.035 ml, 40 mg, 0.37 mmol) dropwise, and further stirred at 0° C. for 10 minutes. The solvent was evaporated, the residue diluted with ethyl acetate, the organic phase washed with water and brine, dried over sodium sulfate and concentrated. The gummy residue was triturated in cyclohexane and diethyl ether, stirred at room temperature, filtered and dried. Yield: 100 mg of carbonic acid ethyl ester 3-methoxy-9-oxo-8-(2,4,6-trimethyl-phenyl)-2,3,4,5-tetrahydro-1H,9H-pyrazolo[1,2-a][1,2,5]triazepin-7-yl ester (title compound P1.2) as a pale yellow solid.

Workup

  1. stirringfurther stirred at 0° C. for 10 minutes
  2. customThe solvent was evaporated
  3. additionthe residue diluted with ethyl acetate
  4. washthe organic phase washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe gummy residue was triturated in cyclohexane
  8. stirringdiethyl ether, stirred at room temperature
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-ed890791412249ab8bb781b0334e5486
Source dataset
uspto-grants-2016_03
Patent number
US09282743B2

Reaction notes

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