Water → HCID 87426603, compound

HRID 623482Notes

Reaction equation

HRID 623482 reaction equation
Cl[C:2]1[N:15]=[C:14]([O:16][CH2:17][C:18]([F:21])([F:20])[F:19])[CH:13]=[CH:12][C:3]=1[C:4]([O:6][CH2:7][C:8]([F:11])([F:10])[F:9])=[O:5].[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.C(N(CC)CC)C.O>O1CCCC1>[O:25]1[CH2:26][CH2:27][N:22]([C:2]2[N:15]=[C:14]([O:16][CH2:17][C:18]([F:21])([F:20])[F:19])[CH:13]=[CH:12][C:3]=2[C:4]([O:6][CH2:7][C:8]([F:11])([F:10])[F:9])=[O:5])[CH2:23][CH2:24]1

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 8471TriethylamineHCID 87426801HCID 87426801, compound

Product 1

HCID 87426603HCID 87426603, compoundYield 101.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2,2,2-trifluoroethyl 2-chloro-6-(2,2,2-trifluoroethoxy)nicotinate (0.30 g, 0.89 mmol, Step-1), morpholine (0.77 mL, 8.89 mmol) and triethylamine (0.62 mL, 4.44 mmol) in tetrahydrofuran (2 mL) is stirred at 140° C. for 10 minutes under microwave irradiation. The reaction mixture is poured into water and extracted with ethyl acetate and dried over sodium sulfate and concentrated in vacuo to give 0.35 g (>99% yield) of the title compound as a yellow solid. This material is used for the next reaction (Step-3) without further purification.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b3c9891833554acb955e8e87c6b125e4
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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