Potassium bis(trimethylsilyl)amide → HCID 68352309, compound

HRID 2174562Notes

Reaction equation

HRID 2174562 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([C:9]2[CH:14]=[CH:13][C:12]([N:15]([CH3:17])[CH3:16])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:18]([O:20]C)=O.[CH3:22][C:23]1[CH:27]=[CH:26][N:25]([CH2:28][C:29](OCC)=[O:30])[N:24]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+]>C1COCC1>[Cl:8][C:6]1[CH:7]=[C:2]2[C:3]([C:18]([OH:20])=[C:28]([N:25]3[CH:26]=[CH:27][C:23]([CH3:22])=[N:24]3)[C:29](=[O:30])[NH:1]2)=[CH:4][C:5]=1[C:9]1[CH:10]=[CH:11][C:12]([N:15]([CH3:16])[CH3:17])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 4578874Ethyl 3-methyl-1H-pyrazole-1-acetateHCID 68352236HCID 68352236, compound2×

Product 1

HCID 68352309HCID 68352309, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 4-amino-6-chloro-4′-(dimethylamino)-[1,1′-biphenyl]-3-carboxylate, (Intermediate 47) (416 mg, 1.365 mmol) and ethyl 2-(3-methyl-1H-pyrazol-1-yl)acetate (Alinda Chemical Ltd, 275 mg, 1.638 mmol) in THF (8.4 mL) stirred under nitrogen at room temperature was added KHMDS 1M/THF (4.09 mL, 4.09 mmol) The reaction mixture was stirred at room temperature for 20 min before being quenched with MeOH, evaporated in vacuo and taken up in water (10 mL). The aqueous layer was acidified to pH=6-7 and filtered. The precipitate obtained was washed with acetonitrile, then with diisopropyl ether and filtered to give the title compound 7-chloro-6-(4-(dimethylamino)phenyl)-4-hydroxy-3-(3-methyl-1H-pyrazol-1-yl)quinolin-2(1H)-one (415 mg, 73.2% yield) as a light yellow powder. LCMS: (M+H)+=395; Rt=2.68 min. HRMS: calculated for C21H20ClN4O2 (M+H)+: 395.1275. found: 395.1283.

Workup

  1. custombefore being quenched with MeOH
  2. customevaporated in vacuo
  3. filtrationfiltered
  4. customThe precipitate obtained
  5. washwas washed with acetonitrile
  6. filtrationwith diisopropyl ether and filtered

Sources & evidence

ORD record
ord-75b762c83da74100ad9d8b0480ee6983
Source dataset
uspto-grants-2015_06
Patent number
US09061998B2

Reaction notes

Loading…