Hydrochloric Acid → 5-(5-Ethyl-1H-pyrazol-4-yl)-N-(4-morpholinophenyl)-[1,2,4]triazolo[1,5-a]pyrazin-8-amine

HRID 1783948Notes

Reaction equation

HRID 1783948 reaction equation
[CH2:1]([C:3]1[N:7](C2CCCCO2)[N:6]=[CH:5][C:4]=1[C:14]1[N:19]2[N:20]=[CH:21][N:22]=[C:18]2[C:17]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)=[CH:26][CH:25]=2)=[N:16][CH:15]=1)[CH3:2].C(C1C(C2N3N=CN=C3C(NC3C=CC(N4CCOCC4)=CC=3)=NC=2)=CN(C2CCCCO2)N=1)C.Cl>CO>[CH2:1]([C:3]1[NH:7][N:6]=[CH:5][C:4]=1[C:14]1[N:19]2[N:20]=[CH:21][N:22]=[C:18]2[C:17]([NH:23][C:24]2[CH:25]=[CH:26][C:27]([N:30]3[CH2:31][CH2:32][O:33][CH2:34][CH2:35]3)=[CH:28][CH:29]=2)=[N:16][CH:15]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 57590055{5-[3-ethyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazol-4-yl]-[1,2,4]triazolo[1,5-a]pyrazin-8-yl}-(4-morpholin-4-yl-phenyl)-amineHCID 57590067{5-[5-ethyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazol-4-yl]-[1,2,4]triazolo[1,5-a]pyrazin-8-yl}-(4-morpholin-4-yl-phenyl)-amine

Product 1

HCID 1359003615-(5-Ethyl-1H-pyrazol-4-yl)-N-(4-morpholinophenyl)-[1,2,4]triazolo[1,5-a]pyrazin-8-amineYield 17%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of {5-[5-ethyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazol-4-yl]-[1,2,4]triazolo[1,5-a]pyrazin-8-yl}-(4-morpholin-4-yl-phenyl)-amine and {5-[3-ethyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazol-4-yl]-[1,2,4]triazolo[1,5-a]pyrazin-8-yl}-(4-morpholin-4-yl-phenyl)-amine (40 mg, 0.077 mmol) and conc. HCl (0.3 mL) in MeOH (10 mL) is stirred at room temperature for 5 hours. After removing the solvent, the solid residue is partitioned between ethyl acetate and sat. NaHCO3. The undissolved solid is collected by filtration, washed with water, diethyl ether and petroleum ether and dried to afford the title compound (5 mg, 17%). Conversion into the mesylate salt using 0.1M methanesulfonic acid (0.128 mL) affords the title compound (5.6 mg, 89%) as a solid.

Workup

  1. customAfter removing the solvent
  2. customthe solid residue is partitioned between ethyl acetate and sat. NaHCO3
  3. filtrationThe undissolved solid is collected by filtration
  4. washwashed with water, diethyl ether and petroleum ether
  5. customdried

Sources & evidence

ORD record
ord-bec95c032eb84b4ca0472d157d283fe2
Source dataset
uspto-grants-2009_03
Patent number
US07501411B2

Reaction notes

Loading…