1,2-Dichloroethane → HCID 16064898, compound

HRID 1360688Notes

Reaction equation

HRID 1360688 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]2[C:15]([CH:16]=[CH:17][CH:18]=1)=[C:14]([C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][C:27]=1[F:28])[C:22](O)=[O:23])[C:13](=[O:29])[CH:12]=[CH:11]2.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.O[NH:45][C:46](=[NH:48])[CH3:47]>C(#N)C.CCOC(C)=O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]2[C:15]([CH:16]=[CH:17][CH:18]=1)=[C:14]([C:19]1[CH:20]=[C:21]([C:22]3[O:23][N:48]=[C:46]([CH3:47])[N:45]=3)[CH:25]=[CH:26][C:27]=1[F:28])[C:13](=[O:29])[CH:12]=[CH:11]2

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 16064758HCID 16064758, compoundHCID 178465666HCID 178465666, compound

Product 1

HCID 16064898HCID 16064898, compoundYield 28.8%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-[6-(2,4-difluorophenyl)-2-oxo-2H-quinolizin-1-yl]-4-fluorobenzoic acid (Example 31, 50 mg, 0.12 mmol) in acetonitrile (1.2 mL) was added EDC (48 mg, 0.25 mmol), and HOBt (34 mg, 0.25 mmol). The reaction was stirred at room temperature for 1 hour and then N-hydroxyethanimidamide (46.6 mg, 0.63 mmol) was added. The reaction was heated to 90° C. for 18 hours and then cooled to room temperature. The mixture was diluted with EtOAc washed with aqueous NH4Cl, 0.5 N HCl, water, brine, dried over MgSO4, and concentrated. The crude material was purified via silica gel chromatography (100% EtOAc to give the title compound as a light yellow solid (15 mg).

Workup

  1. temperatureThe reaction was heated to 90° C. for 18 hours
  2. temperaturecooled to room temperature
  3. washwashed with aqueous NH4Cl, 0.5 N HCl, water, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe crude material was purified via silica gel chromatography (100% EtOAc

Sources & evidence

ORD record
ord-819556df46d9410fb347bf1e75ba6dc2
Source dataset
uspto-grants-2011_02
Patent number
US07879875B2

Reaction notes

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