Hydrochloric Acid → HCID 67009139, compound

HRID 519733Notes

Reaction equation

HRID 519733 reaction equation
[N:1]1[N:2]=[C:3]([NH:6][CH:7]2[CH2:10][CH:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:8]2)[NH:4][CH:5]=1.[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH:31]([C:37](=O)[CH2:38][CH2:39][CH3:40])[C:32](OCC)=[O:33])=[C:26]([F:42])[CH:25]=1)#[N:17].C(N(CC)C1C=CC=CC=1)C.Cl>>[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31]2[C:32](=[O:33])[N:6]([CH:7]3[CH2:8][CH:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:10]3)[C:3]3[N:2]([N:1]=[CH:5][N:4]=3)[C:37]=2[CH2:38][CH2:39][CH3:40])=[C:26]([F:42])[CH:25]=1)#[N:17]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7061N,N-DiethylanilineHCID 57460949Ethyl 2-[(2'-cyano-3-fluorobiphenyl-4-yl)methyl]-3-oxohexanoateHCID 178469197HCID 178469197, compound

Product 1

HCID 67009139HCID 67009139, compoundYield 41%

Conditions

Temperature
180 °C

Procedure

A mixture of ethyl 3-(4H-1,2,4-triazol-3-ylamino)cyclobutanecarboxylate (4.0 g), ethyl 2-[(2′-cyano-3-fluorobiphenyl-4-yl)methyl]-3-oxohexanoate (12 g) and N,N-diethylaniline (15 mL) was stirred at 180° C. for 48 hr and then at room temperature for 38 hr. The reaction mixture was added to 1 M hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with 1 M hydrochloric acid and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (4.0 g, 41%).

Workup

  1. waitat room temperature for 38 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with 1 M hydrochloric acid
  4. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2cbe4ec536b7425f9e882a61b346ad0f
Source dataset
uspto-grants-2015_08
Patent number
US09115136B2

Reaction notes

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