Acetic Anhydride → HCID 59551680, compound

HRID 657271Notes

Reaction equation

HRID 657271 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 59551680HCID 59551680, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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)+.

Workup

  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)

Sources & evidence

ORD record
ord-38d964d2ea5249b48a4a1fa9151b9cf5
Source dataset
uspto-grants-2011_12
Patent number
US08071768B2

Reaction notes

Loading…