Acetic Anhydride → HCID 117933014, compound

HRID 1477643Notes

Reaction equation

HRID 1477643 reaction equation
[NH2:1][CH:2]1[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:5][CH:4]=[C:3]1[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1.C(N(CC)CC)C.[C:29](OC(=O)C)(=[O:31])[CH3:30]>CN(C)C1C=CN=CC=1.O1CCCC1>[C:29]([NH:1][CH:2]1[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:5][CH:4]=[C:3]1[C:15]1[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=1)(=[O:31])[CH3:30]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 117839662HCID 117839662, compound

Product 1

HCID 117933014HCID 117933014, compoundYield 104.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a tetrahydrofuran solution (2.0 ml) of tert-butyl 5-amino-4-(4-fluorophenyl)-5,6-dihydropyridine-1(2H)-carboxylate (100 mg, 0.342 mmol) synthesized in Reference Synthesis Example 202, triethylamine (52.0 μL, 0.374 mmol) and 4-dimethylaminopyridine (2.08 mg, 0.0170 mmol) were added and then acetic anhydride (26.0 μL, 0.374 mmol) was added with stirring at 0° C., followed by stirring the resultant reaction solution at 0° C. for 2 hours. After completion of the reaction, the reaction solution was purified by silica gel column chromatography to obtain the title compound (119 mg, yield 87%).

Workup

  1. additionwere added
  2. stirringby stirring the resultant
  3. customreaction solution at 0° C. for 2 hours
  4. customAfter completion of the reaction
  5. customthe reaction solution was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-99a9db030e5f4857b8cd3d7b8501f727
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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