Ethyl orthoformate → HCID 59793745, compound

HRID 736165Notes

Reaction equation

HRID 736165 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[C:6]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)=[O:9])[CH:7]=1.[CH2:32](OC(OCC)OCC)C.[N-:42]=[N+:43]=[N-:44].[Na+]>C(O)(=O)C.O.[OH-].[Na+]>[N:26]1([C:5]2[CH:4]=[CH:3][C:2]([N:1]3[CH:32]=[N:44][N:43]=[N:42]3)=[CH:7][C:6]=2[C:8]([N:10]2[CH2:11][CH2:12][N:13]([C:16]3[CH:17]=[CH:18][C:19]([C:22]([F:24])([F:25])[F:23])=[CH:20][CH:21]=3)[CH2:14][CH2:15]2)=[O:9])[CH2:27][CH2:28][O:29][CH2:30][CH2:31]1

Participants

7

Reactant 3

HCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 59793630HCID 59793630, compound

Product 1

HCID 59793745HCID 59793745, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
75 °C

Procedure

A suspension of (5-Amino-2-morpholin-4-yl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone (50 mg, 0.115 mmol) in Acetic acid (1 ml) was heated to 75° C. under nitrogen and then triethylorthoformate (36.76 ul, 0.34 mmol) was slowly added. After 1 hour, sodium azide (22.4 mg, 0.34 mmol) was added portionwise and the reaction mixture was stirred at 75° C. for 1 h30. The reaction mixture was cooled to room temperature, diluted with water and basified with 1N NaOH solution. The aqueous phase was extracted with ethyl acetate. The organic phases were combined, dried over Na2SO4, filtered and evaporated to dryness. The residue was chromatographed on silica gel: Eluent: Heptane/Ethylacetate 0% to 60% (10 minutes) to provide the title compound (29 mg, 52%) as yellow solid, MS (m/e): 488.2 (M+H+, 100%)

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-dc84286959a24413af117ef0fce2cafe
Source dataset
uspto-grants-2009_09
Patent number
US07595314B2

Reaction notes

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