Water → HCID 86655407、化合物

HRID 2190480ノート

反応式

HRID 2190480 の反応式
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]3[CH:13]=[C:14]([NH:19][C:20](=[O:33])[C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([C:30]#[N:31])([CH3:29])[CH3:28])[C:22]=4[Cl:32])[CH:15]=[CH:16][C:17]=3[F:18])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH:34]1([C:37](Cl)=[O:38])[CH2:36][CH2:35]1.N1C=CC=CC=1.O>O1CCCC1.C(OCC)(=O)C>[Cl:32][C:22]1[C:23]([C:27]([C:30]#[N:31])([CH3:29])[CH3:28])=[CH:24][CH:25]=[CH:26][C:21]=1[C:20]([NH:19][C:14]1[CH:15]=[CH:16][C:17]([F:18])=[C:12]([O:11][C:9]2[CH:8]=[CH:7][C:5]3[N:6]=[C:2]([NH:1][C:37]([CH:34]4[CH2:36][CH2:35]4)=[O:38])[S:3][C:4]=3[CH:10]=2)[CH:13]=1)=[O:33]

参加物

7

反応物 4

HCID 962WaterHCID 1049PyridineHCID 77637Cyclopropanecarbonyl chlorideHCID 86655406N-{3-[(2-amino-1,3-benzothiazol-6-yl)oxy]-4-fluorophenyl}-2-chloro-3-(1-cyano-1-methylethyl)benzamide

生成物 1

HCID 86655407HCID 86655407、化合物収率 40.4%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of N-{3-[(2-amino-1,3-benzothiazol-6-yl)oxy]-4-fluorophenyl}-2-chloro-3-(1-cyano-1-methylethyl)benzamide (350 mg, 0.73 mmol) produced in Example A47(ii) in tetrahydrofuran (20 mL) were added cyclopropanecarbonyl chloride (114 mg, 1.09 mmol) and pyridine (86 mg, 1.09 mmol), and the mixture was stirred at room temperature for 30 min. Water (100 mL) and ethyl acetate (100 mL) were added to the reaction mixture, and the mixture was stirred for 30 min. The organic layer was separated, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=20/80→0/100), and triturated with ethyl acetate/hexane to give the title compound (162 mg, 40%) as a colorless solid.

後処理

  1. stirringthe mixture was stirred for 30 min
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe insoluble material was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate=20/80→0/100)
  7. customtriturated with ethyl acetate/hexane

出典と根拠

ORDレコード
ord-78d75b5ffbe84736a4d0058a44bad5e0
出典データセット
uspto-grants-2012_12
特許番号
US08324395B2

反応ノート

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