Cesium carbonate → HCID 11190126, compound

HRID 2373906Notes

Reaction equation

HRID 2373906 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+].[Br:28][C:29]1[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=1[CH2:31]Br>CN(C=O)C>[Br:28][C:29]1[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=1[CH2:31][O:17][C:13]1[CH:12]=[C:11]([C:10]2[N:9]=[C:8]([CH:18]3[CH2:21][CH2:20][CH2:19]3)[N:4]3[CH:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]=23)[CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 769652-Bromobenzyl bromideHCID 11716093HCID 11716093, compound

Product 1

HCID 11190126HCID 11190126, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3-(8-Amino-3-cyclobutyl-imidazo[1,5-a]pyrazin-1-yl)-phenol (100 mg, 0.36 mmol) in DMF (1.8 mL) was charged with Cs2CO3 (174 mg, 0.54 mmol) and stirred at rt for 30 min. A solution of 2-bromobenzyl bromide (89.2 mg, 0.36 mmol) in DMF was added to the reaction mixture. Reaction mixture was stirred overnight at rt under nitrogen. The crude product was left under high vacuum to remove the DMF for 2 h. The product was then purified by silica gel column chromatography (3% NH3 in MeOH):CH2Cl2 to yield the title compound as a brown/red solid; 1H NMR (CDCl3, 400 MHz) δ 2.02-2.08 (m, 1H), 2.14-2.21 (m, 1H), 2.45-2.53 (m, 2H), 2.59-2.69 (m, 2H), 3.77-3.85 (m, 1H), 5.21 (s, 2H), 7.00 (d, J=5.6 Hz, 1H), 7.04-7.07 (m, 1H), 7.11 (d, J=5.2 Hz, 1H), 7.18-7.23 (m, 1H), 7.25-7.30 (m, 2H), 7.33-7.37 (m, 1H), 7.42 (t, J=16 Hz, 1H), 7.55-7.61 (m, 2H); MS (ES+): m/z 450.81 (100) [MH+].

Workup

  1. customReaction mixture
  2. stirringwas stirred overnight at rt under nitrogen
  3. customto remove the DMF for 2 h
  4. customThe product was then purified by silica gel column chromatography (3% NH3 in MeOH)

Sources & evidence

ORD record
ord-fc5c131e3be94ce88b280b1cb4bbf7d3
Source dataset
uspto-grants-2008_12
Patent number
US07459554B2

Reaction notes

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