HCID 11773105, compound → HCID 11716093, compound

HRID 2373889Notes

Reaction equation

HRID 2373889 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:15]2[N:16]=[C:17]([CH:25]3[CH2:28][CH2:27][CH2:26]3)[N:18]3[CH:23]=[CH:22][N:21]=[C:20]([NH2:24])[C:19]=23)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>Cl.O1CCOCC1>[NH2:24][C:20]1[C:19]2[N:18]([C:17]([CH:25]3[CH2:28][CH2:27][CH2:26]3)=[N:16][C:15]=2[C:11]2[CH:10]=[C:9]([OH:8])[CH:14]=[CH:13][CH:12]=2)[CH:23]=[CH:22][N:21]=1

Participants

4

Reactant 1

HCID 11773105HCID 11773105, compound

Product 1

HCID 11716093HCID 11716093, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1-(3-Benzyloxy-phenyl)-3-cyclobutyl-imidazo[1,5-a]pyrazin-8-ylamine (1.82 g, 4.92 mmol) in 4M HCl in dioxane (20 mL) was heated to 75° C. in a sealed tube for 1.5 h. The reaction was allowed to cool to rt, the dioxane was decanted off and the brown gum residue was cooled to 0° C. in an ice-bath and charged with 7N NH3 in MeOH until basic. The reaction mixture was concentrated in vacuo, triturated with EtOAc and CHCl3, and the NH4Cl salts filtered off. The filtrate was concentrated in vacuo and purified by flash silica chromatography (8% MeOH in CHCl3) resulting in an off-white solid; 1H NMR (DMSO-d6, 400 MHz) δ 1.84-1.99 (m, 1H), 2.00-2.16 (m, 1H), 2.34-2.48 (m, 4H), 3.86-4.00 (m, 1H), 6.08 (brs, 2H), 6.81 (dd, 1H, J=8.4 Hz, 8.0 Hz), 6.95-7.06 (m, 3H), 7.30 (t, 1H, J=8.4 Hz); 7.41 (d, 1H, J=5.2 Hz), 9.63 (brs, 1H); MS (ES+): m/z 281.39 [MH+].

Workup

  1. customthe dioxane was decanted off
  2. temperaturethe brown gum residue was cooled to 0° C. in an ice-bath
  3. additioncharged with 7N NH3 in MeOH until basic
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. customtriturated with EtOAc and CHCl3
  6. filtrationthe NH4Cl salts filtered off
  7. concentrationThe filtrate was concentrated in vacuo
  8. custompurified by flash silica chromatography (8% MeOH in CHCl3)
  9. customresulting in an off-white solid

Sources & evidence

ORD record
ord-3e846e163b674efebcfdbdf8227679b2
Source dataset
uspto-grants-2008_12
Patent number
US07459554B2

Reaction notes

Loading…