Tetrahydrofuran → HCID 57495633, compound

HRID 1092353Notes

Reaction equation

HRID 1092353 reaction equation
[CH:1]1([NH:4][C:5]2([C:12]#N)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)[CH2:3][CH2:2]1.[CH2:14]([O:16][C:17](=[O:27])[C:18]1[CH:23]=[CH:22][C:21]([N:24]=[C:25]=[O:26])=[CH:20][CH:19]=1)[CH3:15].C(N(CC)CC)C.C1C[O:38]CC1>>[CH2:14]([O:16][C:17](=[O:27])[C:18]1[CH:23]=[CH:22][C:21]([N:24]2[C:12](=[O:38])[C:5]3([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]3)[N:4]([CH:1]3[CH2:3][CH2:2]3)[C:25]2=[O:26])=[CH:20][CH:19]=1)[CH3:15]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 589805Ethyl 4-isocyanatobenzoateHCID 431516641-(Cyclopropylamino)cycloheptanecarbonitrile

Product 1

HCID 57495633HCID 57495633, compound

Procedure

1.62 g (9.08 mmol) of 1-Cyclopropylamino-cycloheptanecarbonitrile and the crude 4-Isocyanato-benzoic acid ethyl ester in 15 ml THF were stirred for 3 h at RT and then 3.8 ml (27.3 mmol) of triethylamin was added. The stirring was continued for 24 h and then the reaction mixture was concentrated under reduced pressure to dryness. To the dry residue was added 17 ml of 2N HCl and 33 ml of Ethanol and the whole was refluxed for 1 h. The reaction mixture was taken up in EtOAc and washed with water. The organic layers were concentrated under reduced pressure and the crude product was purified by chromatography over silica gel with EtOAc/Heptan 1:2 to give 265 mg of pure 4-(1-Cyclopropyl-2,4-dioxo-1,3-diaza-spiro[4.6]undec-3-yl)-benzoic acid ethyl ester. MS (ESI): 357.3 (MH+).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure to dryness
  2. additionTo the dry residue was added 17 ml of 2N HCl and 33 ml of Ethanol
  3. temperaturethe whole was refluxed for 1 h
  4. washwashed with water
  5. concentrationThe organic layers were concentrated under reduced pressure
  6. customthe crude product was purified by chromatography over silica gel with EtOAc/Heptan 1:2

Sources & evidence

ORD record
ord-4beb7c7c99d843d89fd0c5a21eda8195
Source dataset
uspto-grants-2012_03
Patent number
US08129423B2

Reaction notes

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