N,N-Dimethylglycine → HCID 67364388, compound

HRID 245692Notes

Reaction equation

HRID 245692 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][C:4](O)=[O:5].C(N(CC)C(C)C)(C)C.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[Br:39][C:40]1[N:41]=[C:42]([CH:50]2[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]2)[N:43]2[CH:48]=[CH:47][N:46]=[C:45]([CH3:49])[C:44]=12>ClCCl.CN(C)C=O.O>[Br:39][C:40]1[N:41]=[C:42]([CH:50]2[CH2:55][CH2:54][N:53]([C:4](=[O:5])[CH2:3][N:2]([CH3:7])[CH3:1])[CH2:52][CH2:51]2)[N:43]2[CH:48]=[CH:47][N:46]=[C:45]([CH3:49])[C:44]=12

Participants

8

Reactant 4

HCID 673N,N-DimethylglycineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67363964HCID 67363964, compound

Product 1

HCID 67364388HCID 67364388, compoundYield 84.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent3×

Procedure

To N,N-dimethylglycine (0.445 mmol, 45.9 mg) in dichloromethane (1 ml) and N,N-dimethylformamide (0.5 ml). were added N,N-diisopropylethylamine (1.762 mmol, 0.291 ml) and O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (0.617 mmol, 198 mg) and stirred at room temperature for 10 minutes. Then 1-bromo-8-methyl-3-(piperidin-4-yl)imidazo[1,5-a]pyrazine (0.440 mmol, 130 mg) dissolved in dichloromethane (2 ml) and N,N-dimethylformamide (0.5 ml) was added. 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 1-(4-(1-bromo-8-methylimidazo[1,5-a]pyrazin-3-yl)piperidin-1-yl)-2-(dimethylamino)ethanone (141 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-9c3b601890e34d93a3d175cf3c9eea58
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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