2-Propanol, reaction products with ammonia, distn. residues → 4-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)-1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-ol

HRID 62439Notes

Reaction equation

HRID 62439 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([C:12]2([OH:22])[CH2:20][CH2:19][CH2:18][C:17]3[N:16]([CH3:21])[N:15]=[CH:14][C:13]2=3)[N:5]2[CH:10]=[CH:9][N:8]=[C:7](Cl)[C:6]=12.[NH3:23].CC(O)C>>[NH2:23][C:7]1[C:6]2[N:5]([C:4]([C:12]3([OH:22])[CH2:20][CH2:19][CH2:18][C:17]4[N:16]([CH3:21])[N:15]=[CH:14][C:13]3=4)=[N:3][C:2]=2[Br:1])[CH:10]=[CH:9][N:8]=1

Participants

3

Reactant 2

HCID 183319422-Propanol, reaction products with ammonia, distn. residuesHCID 893892654-(1-bromo-8-chloroimidazo[1,5-a]pyrazin-3-yl)-1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-ol

Product 1

HCID 712267804-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)-1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-olYield 88%

Conditions

Temperature
120 °C

Procedure

A mixture of 4-(1-bromo-8-chloroimidazo[1,5-a]pyrazin-3-yl)-1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-ol (860 mg, 2.26 mmol) in NH3/i-PrOH (2N, 25 ml) was added in a sealed tube, and then stirred at 120° C. overnight. After cooling to room temperature, the mixture was filtered and the filtrate was evaporated under reduce pressure. The residue was re-dissolved in DCM, washed with water and brine, dried over MgSO4 and concentrated in vacuo to give 4-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)-1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-ol (720 mg, 88%). MS-ESI (m/z): 363 (M+1)+ (Acq Method: 0-60AB_2 min; Rt: 0.98 min)

Workup

  1. additionwas added in a sealed tube
  2. temperatureAfter cooling to room temperature
  3. filtrationthe mixture was filtered
  4. customthe filtrate was evaporated
  5. dissolutionThe residue was re-dissolved in DCM
  6. washwashed with water and brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-239e54a708414edfbc95eb10851ceb20
Source dataset
uspto-grants-2016_09
Patent number
US09446130B2

Reaction notes

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