Acetic Anhydride → HCID 21865084, compound

HRID 857690Notes

Reaction equation

HRID 857690 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[C:18]([O:20][C:21]3[C:26]4[N:27]=[C:28]([NH2:30])[S:29][C:25]=4[CH:24]=[CH:23][CH:22]=3)[N:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:31](OC(=O)C)(=[O:33])[CH3:32]>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]=[C:11]([C:14]2[CH:19]=[C:18]([O:20][C:21]3[C:26]4[N:27]=[C:28]([NH:30][C:31](=[O:33])[CH3:32])[S:29][C:25]=4[CH:24]=[CH:23][CH:22]=3)[N:17]=[CH:16][N:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 58759725HCID 58759725, compound

Product 1

HCID 21865084HCID 21865084, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

4-[6-(2-Amino-benzothiazol-4-yloxy)-pyrimidin-4-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester, (Example 200), (110 mg, 0.26 mmol) was dissolved in toluene (1.0 mL) and treated with acetic anhydride (100 μL, 1.0 mmol, Aldrich) at room temperature. The reaction mixture was stirred at 90° C. for 30 min. The resulting mixture was allowed to cool to room temperature and the solvents were removed in vacuum. The residue was purified by silica gel chromatography (gradient: 0% to 4.0% MeOH/CH2Cl2) to provide the title compound as a light-yellow foam. MS (ESI, pos. ion) m/z: 468 (M+1), 466 (M−1).

Workup

  1. temperatureto cool to room temperature
  2. customthe solvents were removed in vacuum
  3. customThe residue was purified by silica gel chromatography (gradient: 0% to 4.0% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-68c78b12271e44329aa73eb0fa89e086
Source dataset
uspto-grants-2006_12
Patent number
US07144888B2

Reaction notes

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