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Chloroacetyl chloride → N-[4-chloro-3-({2-[(chloroacetyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)phenyl]-3-(1-cyano-1-methylethyl)benzamide

HRID 1800516
ノート
印刷プレビュー

反応式

HRID 1800516 の反応式
[NH2:1][C:2]1[S:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[C:6]([O:11][C:12]1[CH:13]=[C:14]([NH:19][C:20](=[O:32])[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([C:30]#[N:31])([CH3:29])[CH3:28])[CH:22]=3)[CH:15]=[CH:16][C:17]=1[Cl:18])[N:5]=2.[Cl:33][CH2:34][C:35](Cl)=[O:36]>CN(C)C(=O)C.C(OCC)(=O)C>[Cl:18][C:17]1[CH:16]=[CH:15][C:14]([NH:19][C:20](=[O:32])[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([C:30]#[N:31])([CH3:28])[CH3:29])[CH:22]=2)=[CH:13][C:12]=1[O:11][C:6]1[N:5]=[C:4]2[S:3][C:2]([NH:1][C:35](=[O:36])[CH2:34][Cl:33])=[N:10][C:9]2=[CH:8][CH:7]=1
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 2

HCID 6577Chloroacetyl chlorideHCID 86646013N-{3-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-4-chlorophenyl}-3-(1-cyano-1-methylethyl)benzamide

生成物 1

HCID 86646014N-[4-chloro-3-({2-[(chloroacetyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)phenyl]-3-(1-cyano-1-methylethyl)benzamide

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 31374
Dimethylacetamide
溶媒

実験手順

To a solution of N-{3-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-4-chlorophenyl}-3-(1-cyano-1-methylethyl)benzamide (200 mg, 0.431 mmol) produced in Example C50(v) in N,N-dimethylacetamide (3.0 mL) was added chloroacetyl chloride (75.4 μL, 0.948 mmol), and the mixture was stirred at room temperature for 4 hr. The reaction mixture was diluted with ethyl acetate (20 mL), washed with 5% aqueous sodium hydrogen carbonate solution (20 mL) and saturated brine (20 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give N-[4-chloro-3-({2-[(chloroacetyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)phenyl]-3-(1-cyano-1-methylethyl)benzamide as an oily residue.

後処理

  1. washwashed with 5% aqueous sodium hydrogen carbonate solution (20 mL) and saturated brine (20 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationThe insoluble material was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-1c5355f2b0124acbbae86b7061b18873
出典データセット
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08344135B2

反応ノート

読み込み中…

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