Triethylamine → HCID 178468631, compound

HRID 455957Notes

Reaction equation

HRID 455957 reaction equation
[C:1]([C:5]1[C:6]2[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH3:20])[N:11]([C:21]3[CH:26]=[CH:25][C:24]([C:27]#[CH:28])=[CH:23][CH:22]=3)[C:10](=[O:29])[C:7]=2[NH:8][N:9]=1)([CH3:4])([CH3:3])[CH3:2].Cl[C:31](=[N:37][OH:38])[C:32]([O:34][CH2:35][CH3:36])=[O:33].C(N(CC)CC)C>C1COCC1>[C:1]([C:5]1[C:6]2[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH3:20])[N:11]([C:21]3[CH:26]=[CH:25][C:24]([C:27]4[O:38][N:37]=[C:31]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:28]=4)=[CH:23][CH:22]=3)[C:10](=[O:29])[C:7]=2[NH:8][N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 6816376Ethyl chloro(hydroximino)acetate2×HCID 178436510HCID 178436510, compound

Product 1

HCID 178468631HCID 178468631, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

To a mixture of 3-t-butyl-5-(4-ethynylphenyl)-4-(2-methoxyphenyl)-4,5-dihydro-1H-pyrrolo[3,4-c]pyrazol-6-one (1.51 g, 3.9 mmol), ethyl 2-chloro-2-hydroxyiminoacetate (1.19 g, 7.8 mmol) and THF (4 mL), triethylamine (1.09 mL, 7.8 mmol) in THF (3 mL) was added dropwise under ice-cooling conditions, and the mixture was stirred at 0° C. for 4 hr. Ethyl 2-chloro-2-hydroxyiminoacetate (1.19 g, 7.8 mmol) was added, and further triethylamine (0.81 mL, 5.9 mmol) in THF (3 mL) was added dropwise. The mixture was stirred at 0° C. for 2 hr and left stand overnight. The precipitate was removed by filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/n-hexane) to give 3-t-butyl-5-[4-(3-ethoxycarbonyl-5-isoxazolyl)phenyl]-4-(2-methoxyphenyl)-4,5-dihydro-1H-pyrrolo[3,4-c]-pyrazol-6-one (1.26 g, 64%) as a colorless solid.

Workup

  1. additionwas added dropwise under ice-
  2. temperaturecooling conditions
  3. stirringThe mixture was stirred at 0° C. for 2 hr
  4. waitleft
  5. waitstand overnight
  6. customThe precipitate was removed by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-53c2f14da8ae4296b822374d64cd1982
Source dataset
uspto-grants-2013_07
Patent number
US08497263B2

Reaction notes

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