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Potassium Carbonate → tert-Butyl 5-amino-2-methylthio-4-(3-(2-(pyrrolidin-1-yl)-ethoxy)-phenyl)-quinazoline-6-carboxamide

HRID 1766087
ノート
印刷プレビュー

反応式

HRID 1766087 の反応式
C([O-])([O-])=O.[K+].[K+].Cl.Cl[CH2:9][CH2:10][N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1.[C:16]([C:20]1[CH:29]=[C:28]2[C:23]([C:24]([C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([OH:38])[CH:33]=3)=[N:25][C:26]([S:30][CH3:31])=[N:27]2)=[C:22]([NH2:39])[C:21]=1[C:40]([NH2:42])=[O:41])([CH3:19])([CH3:18])[CH3:17]>CC(C)=O>[C:16]([C:20]1[CH:29]=[C:28]2[C:23]([C:24]([C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH2:9][CH2:10][N:11]4[CH2:15][CH2:14][CH2:13][CH2:12]4)[CH:33]=3)=[N:25][C:26]([S:30][CH3:31])=[N:27]2)=[C:22]([NH2:39])[C:21]=1[C:40]([NH2:42])=[O:41])([CH3:19])([CH3:17])[CH3:18]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 816681-(2-Chloroethyl)pyrrolidine hydrochlorideHCID 21109116tert-Butyl 5-amino-2-methylthio-4-(3-hydroxyphenyl)-quinazoline-6-carboxamide

生成物 1

HCID 21109110tert-Butyl 5-amino-2-methylthio-4-(3-(2-(pyrrolidin-1-yl)-ethoxy)-phenyl)-quinazoline-6-carboxamide

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A mixture of K2CO3 (1.0 g), 1-(2-chloroethyl)pyrrolidine hydrochloride (66 mg) and tert-butyl 5-amino-2-methylthio-4-(3-hydroxyphenyl)-quinazoline-6-carboxamide (example 26a, 121 mg) in acetone was heated overnight at reflux. The mixture was cooled to room temperature, the solids were removed by filtration and the filtrate concentrated under reduced pressure. The residue was taken up in EtOAc and washed with water and brine. The organic phase was dried (MgSO4) and concentrated in vacuo. The title compound was purified by HPLC using a Luna C-18 column with the following gradient: 10% aq. CH3CN/CH3CN/0.1% aq. TFA=72/25/3 to 27/70/3 (v/v/v) in 30 min. The title compound was lyophilized from a nixture of water, TFA is and CH3CN.

後処理

  1. temperaturewas heated overnight
  2. temperatureat reflux
  3. customthe solids were removed by filtration
  4. concentrationthe filtrate concentrated under reduced pressure
  5. washwashed with water and brine
  6. dry with materialThe organic phase was dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe title compound was purified by HPLC

出典と根拠

ORDレコード
ord-85f7e2ba71c345e9b66af5ae84d69418
出典データセット
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07229990B2

反応ノート

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