Hydrochloric Acid → HCID 58137768, compound

HRID 2189455Notes

Reaction equation

HRID 2189455 reaction equation
[F:1][C:2]([F:34])([F:33])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11](=[O:32])[NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:23]3[CH:24]=[CH:25][N:26]=[C:27]([C:28]([O:30]C)=[O:29])[C:22]3=[N:21][N:20]=2)=[CH:15][CH:14]=1.C[Si](C)(C)[O-].[K+].Cl>C1COCC1.CCOC(C)=O>[F:34][C:2]([F:1])([F:33])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11](=[O:32])[NH:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[N:23]3[CH:24]=[CH:25][N:26]=[C:27]([C:28]([OH:30])=[O:29])[C:22]3=[N:21][N:20]=2)=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23668039Potassium trimethylsilanolateHCID 58137771HCID 58137771, compound

Product 1

HCID 58137768HCID 58137768, compoundYield 100.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 3-(4-(3-(2-(trifluoromethoxy)phenyl)ureido) phenyl)-[1,2,4]triazolo[4,3-a]pyrazine-8-carboxylate (61F) (72 mg, 0.152 mmol) in THF (3 mL), was added potassium trimethylsilanolate (78 mg, 0.61 mmol). The mixture was stirred at room temperature for 70 min, and then acidified with 1 N aqueous HCl (0.62 mL). The mixture was diluted with EtOAc, washed with water (3×), brine, and dried over Na2SO4. The solvent was removed in vacuo to yield the title compound as a brown solid (70 mg, 100%). HPLC/MS (Method C): retention time=1.83 min, [M+H]+=459.4.

Workup

  1. washwashed with water (3×), brine
  2. dry with materialdried over Na2SO4
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-8febf86355964a5e97b3edfef08526e4
Source dataset
uspto-grants-2012_12
Patent number
US08324241B2

Reaction notes

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