Potassium bis(trimethylsilyl)amide → HCID 68352309、化合物

HRID 2174562ノート

反応式

HRID 2174562 の反応式
[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

参加物

5

反応物 3

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 4578874Ethyl 3-methyl-1H-pyrazole-1-acetateHCID 68352236HCID 68352236、化合物2 回

生成物 1

HCID 68352309HCID 68352309、化合物収率 73.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-75b762c83da74100ad9d8b0480ee6983
出典データセット
uspto-grants-2015_06
特許番号
US09061998B2

反応ノート

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