Ammonium Chloride → HCID 66826904, compound

HRID 1912469Notes

Reaction equation

[NH4+:1].[Cl-].[Br:3][C:4]1[C:5]([F:22])=[CH:6][C:7]([F:21])=[C:8]([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:9]=1>N.CCO>[Br:3][C:4]1[C:5]([F:22])=[CH:6][C:7]([F:21])=[C:8]([C:10]2([CH3:20])[NH:15][C:14]([NH2:1])=[CH:13][N:12]3[N:17]=[CH:18][CH:19]=[C:11]23)[CH:9]=1

Participants

Conditions

Temperature: 85 °C

Procedure

NH4Cl (0.72 g, 13.4 mmol) was added to a stirred suspension of rac-4-(5-bromo-2,4-difluoro-phenyl)-4-methyl-4,5-dihydro-pyrazolo[1,5-a]pyrazin-6-thione (2.4 g, 6.7 mmol) in ammonia 2 M in EtOH (67 mL) and the mixture was heated at 85° C. for 18 hours. The solvent was removed in vacuo and the residue was suspended 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-(5-bromo-2,4-difluoro-phenyl)-4-methyl-4,5-dihydro-pyrazolo[1,5-a]pyrazin-6-yl-amine (1.8 g, 78% yield) as a yellow solid.

Workup

customThe solvent was removed in vacuo
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-a8f408f742c34878aa4400e88611c335
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609660B2

Reaction notes

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