Cesium carbonate → HCID 67416502, compound

HRID 2373927Notes

Reaction equation

HRID 2373927 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-].[Cs+].[Cs+].[CH3:28][O:29][C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=1)[CH2:33]Br.C([O-])(O)=O.[Na+]>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][CH2:33][C:32]4[CH:35]=[CH:36][CH:37]=[C:30]([O:29][CH3:28])[CH:31]=4)[CH:12]=3)[N:9]=2)[CH2:21][CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 40672073-Methoxybenzyl bromideHCID 11716093HCID 11716093, compound

Product 1

HCID 67416502HCID 67416502, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 3-(8-amino-3-cyclobutyl-imidazo[1,5-a]pyrazin-1-yl)-phenol (28 mg, 0.1 mmol) in anhydrous DMF (1 ml) was added cesium carbonate (49 mg, 0.15 mmol) followed by a solution of 3-methoxybenzyl bromide (20 mg, 0.1 mmol) in DMF (0.5 ml). The reaction was stirred at room temperature overnight. The reaction was poured onto saturated NaHCO3 (10 ml) and extracted with EtOAc (2×10 ml). The combined organics were washed with water (10 ml) and aqueous brine solution (3×10 ml), dried (MgSO4), filtered and concentrated in vacuo, to give 3-cyclobutyl-1-[3-(3-methoxy-benzyloxy)-phenyl]-imidazo[1,5-a]pyrazin-8-ylamine as a brown solid (24.1 mg, 60%): 1H NMR (400 MHz, CDCl3) δ 7.42 (t, 1H, J=7.8 Hz), 7.35-7.27 (m, 3H), 7.13 (d, 1H, J=5.1 Hz), 7.08-7.03 (m, 4H), 6.90 (d, 1H, J=8.6 Hz), 5.17 (s, 2H), 3.84 (s, 3H), 3.86-3.79 (m, 1H, obscured), 2.72-2.62 (m, 2H), 2.56-2.47 (m, 2H), 2.25-2.14 (m, 1H), 2.11-2.02 (m, 1H), 2H not observed (NH2); LCMS (ES+) m/z 401.34 [MH+] at Rt 3.20 min.

Workup

  1. extractionextracted with EtOAc (2×10 ml)
  2. washThe combined organics were washed with water (10 ml) and aqueous brine solution (3×10 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-85bfe217ac6248e493fecd28203ec3e2
Source dataset
uspto-grants-2008_12
Patent number
US07459554B2

Reaction notes

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