Diisopropylethylamine → 1-[4-(8-Amino-1-iodo-imidazo[1,5-a]pyrazin-3-yl)-piperidin-1-yl]-2-dimethylamino-ethanone

HRID 449007Notes

Reaction equation

HRID 449007 reaction equation
[I: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]([NH2:11])[C:6]=12.[CH3:18][N:19]([CH2:21][C:22](Cl)=[O:23])[CH3:20].CCN(C(C)C)C(C)C>CN(C=O)C.C([O-])(O)=O.[Na+]>[NH2:11][C:7]1[C:6]2[N:5]([C:4]([CH:12]3[CH2:17][CH2:16][N:15]([C:22](=[O:23])[CH2:21][N:19]([CH3:20])[CH3:18])[CH2:14][CH2:13]3)=[N:3][C:2]=2[I:1])[CH:10]=[CH:9][N:8]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 70103442-(Dimethylamino)acetyl chlorideHCID 669156041-Iodo-3-piperidin-4-yl-imidazo[1,5-a]pyrazin-8-ylamine

Product 1

HCID 690149561-[4-(8-Amino-1-iodo-imidazo[1,5-a]pyrazin-3-yl)-piperidin-1-yl]-2-dimethylamino-ethanone

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred mixture of 1-iodo-3-piperidin-4-yl-imidazo[1,5-a]pyrazin-8-ylamine (1.000 g, 2.91 mmol) and dimethylamino-acetyl chloride (0.38967 g, 3.20 mmol) in DMF (10.00 mL) was added DIEA (2.58 mL, 14.57 mmol) at 0° C. The resulting mixture was stirred at rt. overnight. The mixture was diluted with sat. aq. NaHCO3 and extracted with DCM (50 ml×3). The extracts were combined, dried (Na2SO4). Solvent was then removed under reduced pressure and the resulting residue was used for next step without further purifications. MS (ES+): m/z 428.74 [MH+].

Workup

  1. customovernight
  2. extractionextracted with DCM (50 ml×3)
  3. dry with materialdried (Na2SO4)
  4. customSolvent was then removed under reduced pressure

Sources & evidence

ORD record
ord-60fec79f35e04b6c983c1a0f0295dfc4
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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