HCID 178501052, compound → HCID 178501050, compound

HRID 2373891Notes

Reaction equation

HRID 2373891 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]2[N:15]3[CH:16]=[CH:17][N:18]=[C:19]([NH2:20])[C:14]3=[C:13]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27]CC4C=CC=CC=4)[CH:22]=3)[N:12]=2)[CH2:7][CH2:6]1)=[O:4]>Cl.O1CCOCC1>[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]2[N:15]3[CH:16]=[CH:17][N:18]=[C:19]([NH2:20])[C:14]3=[C:13]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=3)[N:12]=2)[CH2:7][CH2:6]1)=[O:4]

Participants

4

Reactant 1

HCID 178501052HCID 178501052, compound

Product 1

HCID 178501050HCID 178501050, compoundYield 196%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of trans-4-[8-Amino-1-(3-benzyloxy-phenyl)-imidazo[1,5-a]pyrazin-3-yl]-cyclohexanecarboxylic acid methyl ester (50 mg, 0.110 mmol) in 4M HCl in dioxane (2 mL) was heated to 75° C. in a oil-bath for ˜2 h. The reaction mixture was allowed to cool to rt, the dioxane was decanted off and the reaction mixture was quenched with 7N NH3 in MeOH solution (˜2 mL). This crude mixture was concentrated in vacuo resulting in 79 mg of an off-white solid (containing NH4Cl salts). The crude material was purified by flash silica chromatography (10% 7N NH3 in MeOH in CHCl3) resulting in an off-white solid; 1H NMR (DMSO-d6, 400 MHz) δ 1.51-1.78 (m, 4H), 1.95-2.08 (m, 4H), 2.38-2.48 (m, 1H), 3.07-3.20 (m, 1H), 3.63 (s, 3H), 6.06 (brs, 2H), 6.76-6.89 (m, 1H), 6.95-7.05 (m, 3H), 7.29 (t, 1H, J=7.8 Hz), 7.65 (d, 1H, J=5.1 Hz), 9.62 (brs, 1H); MS (ES+): m/z 367.26 [MH+].

Workup

  1. customthe dioxane was decanted off
  2. customthe reaction mixture was quenched with 7N NH3 in MeOH solution (˜2 mL)
  3. concentrationThis crude mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-fc3a56485caf48d995e85269237d73f5
Source dataset
uspto-grants-2008_12
Patent number
US07459554B2

Reaction notes

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