Acetic Anhydride → HCID 59551680、化合物

HRID 657271ノート

反応式

HRID 657271 の反応式
[C:1](OC(=O)C)(=[O:3])[CH3:2].[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([C:21]2[C:30]3[C:25](=[CH:26][C:27]([O:31][CH:32]4[CH2:35][NH:34][CH2:33]4)=[CH:28][CH:29]=3)[N:24]=[CH:23][N:22]=2)[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]>C(Cl)Cl>[C:8]([O:12][C:13]([N:15]1[CH2:16][CH2:17][CH:18]([C:21]2[C:30]3[C:25](=[CH:26][C:27]([O:31][CH:32]4[CH2:33][N:34]([C:1](=[O:3])[CH3:2])[CH2:35]4)=[CH:28][CH:29]=3)[N:24]=[CH:23][N:22]=2)[CH2:19][CH2:20]1)=[O:14])([CH3:11])([CH3:9])[CH3:10]

参加物

4

反応物 2

HCID 7918Acetic AnhydrideHCID 595517494-[7-(Azetidin-3-yloxy)-quinazolin-4-yl]-piperidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 59551680HCID 59551680、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Acetic anhydride (66 μL, 703 μmol) was added dropwise with stirring at rt to a mixture of 4-[7-(Azetidin-3-yloxy)-quinazolin-4-yl]-piperidine-1-carboxylic acid tert-butyl ester (180 mg, 469 μmol), as prepared in the previous step, in DCM (1.0 mL). The resulting homogeneous yellow solution was stirred overnight, and was then partitioned with DCM (3 mL) and 1M NaHCO3 (1×4 mL). The organic layer was dried (Na2SO4), concentrated, and purified by silica flash chromatography (8:2 DCM/acetone/3% DMEA eluent) to afford the title compound as a white crystalline film (88.3 mg, 44% over two steps). LC/MS (ESI): calcd mass 426.2, found 426.9 (MH)+.

後処理

  1. customwas then partitioned with DCM (3 mL) and 1M NaHCO3 (1×4 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified by silica flash chromatography (8:2 DCM/acetone/3% DMEA eluent)

出典と根拠

ORDレコード
ord-38d964d2ea5249b48a4a1fa9151b9cf5
出典データセット
uspto-grants-2011_12
特許番号
US08071768B2

反応ノート

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