Acetic Anhydride → HCID 58515925, compound

HRID 717861Notes

Reaction equation

HRID 717861 reaction equation
Cl.Cl.[Br:3][C:4]1[C:5]2[N:6]([CH:22]=[N:23][CH:24]=2)[C:7]([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[C:8]([C:10]([N:12]([O:14][CH3:15])[CH3:13])=[O:11])[CH:9]=1.C(N(CC)C(C)C)(C)C.[C:34](OC(=O)C)(=[O:36])[CH3:35]>CN(C)C=O.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[C:34]([N:19]1[CH2:18][CH2:17][N:16]([C:7]2[N:6]3[CH:22]=[N:23][CH:24]=[C:5]3[C:4]([Br:3])=[CH:9][C:8]=2[C:10]([N:12]([O:14][CH3:15])[CH3:13])=[O:11])[CH2:21][CH2:20]1)(=[O:36])[CH3:35]

Participants

7

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 86659299HCID 86659299, compound

Product 1

HCID 58515925HCID 58515925, compoundYield 90.9%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 8-bromo-N-methoxy-N-methyl-5-piperazin-1-ylimidazo[1,5-a]pyridine-6-carboxamide dihydrochloride (500 mg, 1.1 mmol) in N,N-dimethylformamide (5 mL) was treated with N,N-diisopropylethylamine (0.69 mL, 4.0 mmol), followed by 4-dimethylaminopyridine (5 mg, 0.04 mmol). The reaction mixture was treated with acetic anhydride (0.13 mL, 1.4 mmol) dropwise and stirred at 20° C. for 1 hour. The reaction mixture was diluted with ethyl acetate (200 mL), washed with saturated sodium bicarbonate, water (3×), and brine, dried over sodium sulfate, filtered and concentrated to give the desired product (0.41 g, 89%). This material was used without purification. LCMS for C16H21BrN5O3 (M+H)+: m/z=410.1, 412.1. Found: 409.8, 411.8.

Workup

  1. washwashed with saturated sodium bicarbonate, water (3×), and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-af9aeda2b0e94e22a39c8ff63d21ad89
Source dataset
uspto-grants-2015_11
Patent number
US09193721B2

Reaction notes

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