Potassium Carbonate → HCID 11361235, compound

HRID 2373890Notes

Reaction equation

HRID 2373890 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([CH:18]3[CH2:21][CH2:20][CH2:19]3)=[N:9][C:10]=2[C:11]2[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=2)[CH:5]=[CH:6][N:7]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=1>CN(C=O)C>[CH:18]1([C:8]2[N:4]3[CH:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]3=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:29][C:30]4[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=4)[CH:12]=3)[N:9]=2)[CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 11716093HCID 11716093, compound

Product 1

HCID 11361235HCID 11361235, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

An anhydrous DMF (2 mL) solution of 3-(8-amino-3-cyclobutyl-imidazo[1,5-a]pyrazin-1-yl)-phenol (50 mg, 0.179 mmol) and K2CO3 (27 mg, 0.197 mmol) was charged with 1-bromomethyl-4-fluoro-benzene (7) (24 μL, 0.197 mmol) and stirred 12 h at 40° C. The reaction mixture was partitioned between CHCl3 and H2O and separated. The aqueous layer was re-extracted with CHCl3 (3×) and the combined organic fractions were washed with H2O (1×), brine (1×), dried over Na2SO4, filtered and concentrated in vacuo. The crude mixture was purified by MDP resulting in a light tan/waxy solid; 1H NMR (CDCl3, 400 MHz) δ 1.99-2.08 (m, 1H), 2.11-2.25 (m, 1H), 2.44-2.55 (m, 2H), 2.58-2.70 (m, 2H), 3.75-3.88 (m, 1H), 5.06 (brs, 2H), 5.10 (s, 2H), 6.98-7.15 (m, 5H); 7.20-7.34 (m, 3H), 7.35-7.47 (m, 3H); MS (ES+): m/z 389.14.

Workup

  1. customThe reaction mixture was partitioned between CHCl3 and H2O
  2. customseparated
  3. extractionThe aqueous layer was re-extracted with CHCl3 (3×)
  4. washthe combined organic fractions were washed with H2O (1×), brine (1×)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude mixture was purified by MDP
  9. customresulting in a light tan/waxy solid

Sources & evidence

ORD record
ord-7eeb4c7df6b642bdba37385b5c8c9f8b
Source dataset
uspto-grants-2008_12
Patent number
US07459554B2

Reaction notes

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