Water → HCID 53859849, compound

HRID 1739662Notes

Reaction equation

HRID 1739662 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][O:16][C:17]1[C:22]([Cl:23])=[CH:21][C:20]([C:24]([OH:26])=[O:25])=[CH:19][N:18]=1)[C:5]([NH:7][CH3:8])=[O:6].C(N1C=CN=C1)(N1C=CN=C1)=O.[F:39][C:40]([F:44])([F:43])[CH2:41]O.O>C1COCC1>[CH3:1][O:2][N:3]=[C:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][O:16][C:17]1[C:22]([Cl:23])=[CH:21][C:20]([C:24]([O:26][CH2:41][C:40]([F:44])([F:43])[F:39])=[O:25])=[CH:19][N:18]=1)[C:5]([NH:7][CH3:8])=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 64092,2,2-TrifluoroethanolHCID 682631,1'-CarbonyldiimidazoleHCID 53726168HCID 53726168, compound

Product 1

HCID 53859849HCID 53859849, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of Example 38 (0.3 g, 0.79 mmol) was dissolved in THF (10 mL) to which carbonyldiimidazole (0.129 g, 0.79 mmol) was added. The solution was stirred at room temperature for one hour, at which time 2,2,2-trifluoroethanol (10 mL) was added and the solution stirred overnight at room temperature. The solution was poured into 4-5 volumes of water and extracted with Et2O (2×100 mL). The organics were dried over MgSO4 and concentrated to a yellow-brown oil (0.19 g). Crude product was chromatographed using silica gel (230-400 mesh) with descending solvent gradient from 100% petroleum ether to 80/20 petroleum ether/ethyl acetate as the mobile phase. Elution and concentration gave α-(methoxyimino)-N-methyl-2-[[[3-chloro-5-(2,2,2-trifluoroethoxycarbonyl)-2-pyridinyl]oxy]methyl]-benzeneacetamide (0.09 g) as a green oil.

Workup

  1. additionwas added
  2. additionwas added
  3. extractionextracted with Et2O (2×100 mL)
  4. dry with materialThe organics were dried over MgSO4
  5. concentrationconcentrated to a yellow-brown oil (0.19 g)
  6. customCrude product was chromatographed
  7. washElution and concentration

Sources & evidence

ORD record
ord-23a725e480674fd3bef062d54790093c
Source dataset
uspto-grants-1999_10
Patent number
US05968875

Reaction notes

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