Npc316347 → 3-(3-Methyl-4-oxo-5h-2-oxa-1,5,7-triaza-cyclopenta[a]naphthalen-5-yl)-cyclohexanecarboxylic acid ethyl ester

HRID 1823295Notes

Reaction equation

HRID 1823295 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][CH:8]([NH:12][C:13]([C:15]2[C:16]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][C:22]=3F)=[N:17][O:18][C:19]=2[CH3:20])=[O:14])[CH2:7]1)=[O:5])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C>CN(C)C=O>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][CH:8]([N:12]2[C:26]3[C:21](=[CH:22][CH:23]=[N:24][CH:25]=3)[C:16]3=[N:17][O:18][C:19]([CH3:20])=[C:15]3[C:13]2=[O:14])[CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 3280088Npc316347HCID 696527063-{[3-(3-Fluoro-pyridin-4-yl)-5-methyl isoxazole-4-carbonyl]-amino}cyclo-hexanecarboxylic acid ethy ester

Product 1

HCID 696526573-(3-Methyl-4-oxo-5h-2-oxa-1,5,7-triaza-cyclopenta[a]naphthalen-5-yl)-cyclohexanecarboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolve 3-{[3-(3-fluoro-pyridin-4-yl)-5-methyl isoxazole-4-carbonyl]-amino}cyclo-hexanecarboxylic acid ethy ester (0.70 g, 1.87 mmol) in N,N-dimethyl-formamide (10 mL0 at ambient temperature under a nitrogen atmosphere. Add a solution of potassuim bis(trimethylsilyl)amide (0.5 M in toluene, 4.11 mL, 2.06 mmol) and stir for 20 min. at ambient temperature. Quench with water and follow by adding solid sodium chloride. Extract with ethyl acetate and wash the combined extracts with water and dry over sodium sulfate. Concentrate and elute over silica gel using methanol/dichloromethane, allowing for the isolation of 656 mg (99%) of the desired product as a light solid. MS(ES): (M+1)+ 356.2, 357.2 m/z.

Workup

  1. customQuench with water
  2. additionby adding solid sodium chloride
  3. extractionExtract with ethyl acetate
  4. washwash the combined extracts with water
  5. dry with materialdry over sodium sulfate
  6. concentrationConcentrate
  7. washelute over silica gel

Sources & evidence

ORD record
ord-33ae0a8d42464309bd5cf32c4886cc4f
Source dataset
uspto-grants-2006_05
Patent number
US07037921B2

Reaction notes

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