Water → HCID 67363986, compound

HRID 245691Notes

Reaction equation

HRID 245691 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[N:5]2[CH:10]=[CH:9][N:8]=[C:7]([CH3:11])[C:6]=12.C(N(CC)CC)C.Cl[CH2:26][C:27]([N:29]([CH3:31])[CH3:30])=[O:28].O>C1(C)C=CC=CC=1.CN(C)C=O.ClCCl>[Br:1][C:2]1[N:3]=[C:4]([CH:12]2[CH2:17][CH2:16][N:15]([CH2:26][C:27]([N:29]([CH3:31])[CH3:30])=[O:28])[CH2:14][CH2:13]2)[N:5]2[CH:10]=[CH:9][N:8]=[C:7]([CH3:11])[C:6]=12

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 758862-chloro-N,N-dimethylacetamideHCID 67363964HCID 67363964, compound

Product 1

HCID 67363986HCID 67363986, compoundYield 58.8%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To 1-bromo-8-methyl-3-(piperidin-4-yl)imidazo[1,5-a]pyrazine (0.447 mmol, 132 mg) in toluene (1 ml) and N,N-dimethylformamide (1 ml) were added triethylamine (0.894 mmol, 0.125 ml) and 2-chloro-N,N-dimethylacetamide (0.447 mmol, 0.046 ml). After stirring at room temperature for two hours water and dichloromethane were added, mixture was put on a phase separation filter and concentrated in vacuo. Purification by column chromatography (silica gel; dichloromethane with gradient 0 to 20% methanol) gave 2-(4-(1-bromo-8-methylimidazo[1,5-a]pyrazin-3-yl)piperidin-1-yl)-N,N-dimethylacetamide (100 mg).

Workup

  1. additionwere added
  2. custommixture was put on a phase separation
  3. filtrationfilter
  4. concentrationconcentrated in vacuo
  5. customPurification by column chromatography (silica gel; dichloromethane with gradient 0 to 20% methanol)

Sources & evidence

ORD record
ord-3655d727837c496c8f490569efb2135c
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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