Triethylamine → HCID 66591110, compound

HRID 2264670Notes

Reaction equation

HRID 2264670 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][CH2:11][CH:12]2[CH2:16][CH2:15][O:14][CH2:13]2)=[CH:4][C:3]=1[O:17][CH2:18][C:19]([F:22])([F:21])[F:20].C(N(CC)CC)C.[Cl:30][CH2:31][C:32]([N:34]([CH3:36])[CH3:35])=[O:33]>CN(C)C=O>[ClH:30].[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([CH2:11][CH:12]2[CH2:16][CH2:15][O:14][CH2:13]2)[CH2:31][C:32]([N:34]([CH3:36])[CH3:35])=[O:33])=[CH:4][C:3]=1[O:17][CH2:18][C:19]([F:20])([F:21])[F:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 758862-chloro-N,N-dimethylacetamideHCID 59596849HCID 59596849, compound

Product 1

HCID 66591110HCID 66591110, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 85 mg (0.26 mmol) of [2-[4-fluoro-3-(2,2,2-trifluoro-ethoxy)-phenyl]-ethyl]-(tetrahydrofuran-3-ylmethyl)amine, 0.06 ml of triethylamine and 48 mg (0.39 mmol) of 2-chloro-N,N-dimethyl-acetamide in 3 ml of dimethylformamide was heated for 1 hour to 120° C. with microwaves. The solvent was removed under vacuum. The crude product was purified by flash chromatography (dichloromethane/methanol/NH3 100:3:0.3 v:v:v). The product was dissolved in anhydrous hydrochloric acid in ethyl acetate, the solvent was removed under reduced pressure and the product was triturated with diethyl ether. 74 mg (65% yield) of the title compound were isolated as a brown solid.

Workup

  1. temperaturewas heated for 1 hour to 120° C. with microwaves
  2. customThe solvent was removed under vacuum
  3. customThe crude product was purified by flash chromatography (dichloromethane/methanol/NH3 100:3:0.3 v:v:v)
  4. dissolutionThe product was dissolved in anhydrous hydrochloric acid in ethyl acetate
  5. customthe solvent was removed under reduced pressure
  6. customthe product was triturated with diethyl ether

Sources & evidence

ORD record
ord-f123db9f46a34f09b248e4b17ed926dc
Source dataset
uspto-grants-2010_12
Patent number
US07855227B2

Reaction notes

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