Hydrochloric Acid → HCID 135900339, compound

HRID 1783962Notes

Reaction equation

HRID 1783962 reaction equation
C([SiH2][O:6][C:7](C)(C)[C:8]1[C:12]([C:13]2[N:18]3[N:19]=[CH:20][N:21]=[C:17]3[C:16]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([N:29]4[CH2:34][CH2:33][O:32][CH2:31][CH2:30]4)=[CH:25][CH:24]=3)=[N:15][CH:14]=2)=[CH:11][N:10](C2CCCOC2)[N:9]=1)(C)(C)C.C([SiH2]OC(C)(C)C1N(C2CCCOC2)N=CC=1C1N2N=CN=C2C(NC2C=CC(N3CCOCC3)=CC=2)=NC=1)(C)(C)C.Cl>CO>[O:32]1[CH2:31][CH2:30][N:29]([C:26]2[CH:25]=[CH:24][C:23]([NH:22][C:16]3[C:17]4[N:18]([N:19]=[CH:20][N:21]=4)[C:13]([C:12]4[CH:11]=[N:10][NH:9][C:8]=4[CH2:7][OH:6])=[CH:14][N:15]=3)=[CH:28][CH:27]=2)[CH2:34][CH2:33]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 131727354HCID 131727354, compoundHCID 131727355HCID 131727355, compound

Product 1

HCID 135900339HCID 135900339, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of {5-[3-(tert-butyl-dimethyl-silanyloxymethyl)-1-(tetrahydro-pyran-3-yl)-1H-pyrazol-4-yl]-[1,2,4]triazolo[1,5-a]pyrazin-8-yl}-(4-morpholin-4-yl-phenyl)-amine and {5-[5-(tert-butyl-dimethyl-silanyloxymethyl)-1-(tetrahydro-pyran-3-yl)-1H-pyrazol-4-yl]-[1,2,4]triazolo[1,5-a]pyrazin-8-yl}-(4-morpholin-4-yl-phenyl)-amine (53.6 mg, 0.077 mmol) and conc. HCl (0.27 mL) in MeOH (5 mL) is stirred at room temperature for 2 hours. After removing the solvent, the residue is partitioned between ethyl acetate and water. The aqueous layer is washed with ethyl acetate (3×) and the combined organic layers are dried over MgSO4, filtered and concentrated. The residue is dissolved in 4M HCl in dioxane, concentrated in vacuo and then partitioned between ethyl acetate and sat. NaHCO3. The organic layer is dried over MgSO4, filtered and concentrated in vacuo to afford a crude compound purified by silica gel column chromatography. The title compound is isolated eluting with EtOAc and a 95:5 mixture DCM:MeOH (5.4 mg, 18%).

Workup

  1. customAfter removing the solvent
  2. customthe residue is partitioned between ethyl acetate and water
  3. washThe aqueous layer is washed with ethyl acetate (3×)
  4. dry with materialthe combined organic layers are dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe residue is dissolved in 4M HCl in dioxane
  8. concentrationconcentrated in vacuo
  9. custompartitioned between ethyl acetate and sat. NaHCO3
  10. dry with materialThe organic layer is dried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customto afford a crude compound
  14. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-2603bbe820c04d83bd8522fba1cbcf86
Source dataset
uspto-grants-2009_03
Patent number
US07501411B2

Reaction notes

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