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Hydrochloric Acid → 6-Butoxy-2-[4-(3-dimethylaminopyrrolidin-1-yl)-3-fluorophenyl]-2H-isoquinolin-1-one

HRID 69423
ノート
印刷プレビュー

反応式

HRID 69423 の反応式
[CH2:1]([Li])CCC.C(NC(C)C)(C)C.[CH2:13]([O:17][C:18]1[CH:41]=[CH:40][C:21]([C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([N:31]3[CH2:35][CH2:34][CH:33]([N:36]([CH3:38])[CH3:37])[CH2:32]3)=[C:27]([F:39])[CH:26]=2)=[O:23])=[C:20]([CH3:42])[CH:19]=1)[CH2:14][CH2:15][CH3:16].Cl>C1COCC1.CN(C=O)C>[CH2:13]([O:17][C:18]1[CH:19]=[C:20]2[C:21](=[CH:40][CH:41]=1)[C:22](=[O:23])[N:24]([C:25]1[CH:30]=[CH:29][C:28]([N:31]3[CH2:35][CH2:34][CH:33]([N:36]([CH3:38])[CH3:37])[CH2:32]3)=[C:27]([F:39])[CH:26]=1)[CH:1]=[CH:42]2)[CH2:14][CH2:15][CH3:16]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 689905684-butoxy-N-[4-(3-dimethylaminopyrrolidin-1-yl)-3-fluorophenyl]-2-methylbenzamideHCID 178418339Butyllithium

生成物 1

HCID 579167686-Butoxy-2-[4-(3-dimethylaminopyrrolidin-1-yl)-3-fluorophenyl]-2H-isoquinolin-1-one

試薬・触媒・溶媒 2

HCID 6228
Dimethylformamide
溶媒
HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

n-Butyllithium (2.6M in toluene; 0.70 mL) was added to a solution of N,N-diisopropylamine (184 mg) in THF (30 mL) at −78° C. After 10 minutes, 4-butoxy-N-[4-(3-dimethylaminopyrrolidin-1-yl)-3-fluorophenyl]-2-methylbenzamide (0.30 g) was added, and the mixture was stirred at −78° C. for 30 minutes and then warmed to −20° C. DMF (53 mg) was added, and the reaction mixture was hydrolyzed after a further 30 minutes with hydrochloric acid. The reaction mixture was partitioned between sodium carbonate solution and ethyl acetate. The organic phase was dried over sodium sulfate and concentrated. The residue was purified by preparative HPLC. The product with the molecular weight of 423.54 (C25H30FN3O2) was obtained in this way; MS (ESI): 424 (M+H+).

後処理

  1. temperaturewarmed to −20° C
  2. customThe reaction mixture was partitioned between sodium carbonate solution and ethyl acetate
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by preparative HPLC
  6. customThe product with the molecular weight of 423.54 (C25H30FN3O2) was obtained in this way

出典と根拠

ORDレコード
ord-8ba8bc138ec249ef952b5f6c4cd4fac5
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08822495B2

反応ノート

読み込み中…

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