Ammonium Chloride → HCID 66825611, compound

HRID 1912457Notes

Reaction equation

[NH4+:1].[Cl-].[Br:3][C:4]1[CH:5]=[C:6]([C:10]2([CH3:20])[NH:15][C:14](=S)[CH2:13][N:12]3[N:17]=[CH:18][CH:19]=[C:11]23)[CH:7]=[CH:8][CH:9]=1>CCO>[Br:3][C:4]1[CH:5]=[C:6]([C:10]2([CH3:20])[N:15]=[C:14]([NH2:1])[CH2:13][N:12]3[N:17]=[CH:18][CH:19]=[C:11]23)[CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 80 °C

Procedure

NH4Cl (0.15 g, 2.79 mmol) was added to a stirred solution of rac-4-(3-bromo-phenyl)-4-methyl-4,5-dihydro-pyrazolo[1,5-a]pyrazine-6-thione (0.45 g, 1.40 mmol) in EtOH (50 mL) and the mixture was heated at 80° C. for 28 hours. The solvent was removed in vacuo and the residue was dissolved in DCM and washed with water. The organic layer was separated, dried (MgSO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica gel; 7 M solution of ammonia in methanol in AcOEt 0/100 to 20/80). The desired fractions were collected and concentrated in vacuo to yield rac-4-(3-bromo-phenyl)-4-methyl-4,7-dihydro-pyrazolo[1,5-a]pyrazin-6-ylamine (0.42 g, 99% yield) as a yellow solid.

Workup

customThe solvent was removed in vacuo
dissolutionthe residue was dissolved in DCM
washwashed with water
customThe organic layer was separated
dry with materialdried (MgSO4)
filtrationfiltered
customthe solvents evaporated in vacuo
customThe crude product was purified by flash column chromatography (silica gel; 7 M solution of ammonia in methanol in AcOEt 0/100 to 20/80)
customThe desired fractions were collected
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-c608e0fda4d747cbb8b7b8be08c42c9f
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609660B2

Reaction notes

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