Hydrochloric Acid → HCID 60198423, compound

HRID 2174560Notes

Reaction equation

HRID 2174560 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[C:15]=3[OH:22])=[CH:10][CH:9]=2)=[CH:6][C:5]([C:23](OC)=[O:24])=[C:4]([NH:27][C:28](=[O:36])[CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].Cl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([C:23]([OH:24])=[C:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:28](=[O:36])[NH:27]2)=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[C:15]=2[OH:22])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3251421Potassium bis(trimethylsilyl)amideHCID 68352119HCID 68352119, compound2×

Product 1

HCID 60198423HCID 60198423, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 6-chloro-2″-hydroxy-3″-methoxy-4-(2-phenylacetamido)-[1,1′:4′,1″-terphenyl]-3-carboxylate (Intermediate 58) (340 mg, 0.677 mmol) in tetrahydrofuran (100 mL) at 60° C. was added dropwise KHMDS 0.5M/THF (5.42 mL, 2.71 mmol). The reaction mixture was stirred for 2 h after the end of addition. After cooling, the reaction mixture was acidified with 1N HCl and extracted with dichloromethane. The organic layer was washed with brine then dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was taken up in acetonitrile, filtered and was washed with acetonitrile and diisopropylether to give the title compound 7-chloro-4-hydroxy-6-[2′-hydroxy-3′-(methyloxy)-4-biphenylyl]-3-phenyl-2(1H)-quinolinone (175 mg, 0.372 mmol, 55% yield) as a light brown powder. LCMS: (M+H)+=470; Rt=2.99 min. HRMS: calculated for C28H19ClNO4 (M−H)+: 468.1003. found: 468.0962.

Workup

  1. additionafter the end of addition
  2. temperatureAfter cooling
  3. extractionextracted with dichloromethane
  4. washThe organic layer was washed with brine
  5. dry with materialthen dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. filtrationfiltered
  9. washwas washed with acetonitrile and diisopropylether

Sources & evidence

ORD record
ord-757359e0687444afbf30614a1cd70649
Source dataset
uspto-grants-2015_06
Patent number
US09061998B2

Reaction notes

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