Hydrochloric Acid → HCID 53482140, compound

HRID 1990275Notes

Reaction equation

HRID 1990275 reaction equation
Cl.[N:2]1([C:6]([C:8]2[N:9]=[CH:10][C:11]([O:14][C:15]3[CH:16]=[C:17]([CH:28]=[C:29]([O:31][C@@H:32]([CH3:42])[CH2:33][O:34][Si](C(C)(C)C)(C)C)[CH:30]=3)[C:18]([NH:20][C:21]3[CH:26]=[N:25][C:24]([CH3:27])=[CH:23][N:22]=3)=[O:19])=[N:12][CH:13]=2)=[O:7])[CH2:5][CH2:4][CH2:3]1>CO>[N:2]1([C:6]([C:8]2[N:9]=[CH:10][C:11]([O:14][C:15]3[CH:16]=[C:17]([CH:28]=[C:29]([O:31][C@@H:32]([CH3:42])[CH2:33][OH:34])[CH:30]=3)[C:18]([NH:20][C:21]3[CH:26]=[N:25][C:24]([CH3:27])=[CH:23][N:22]=3)=[O:19])=[N:12][CH:13]=2)=[O:7])[CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 536296913-{[5-(azetidin-1-ylcarbonyl)pyrazin-2-yl]oxy}-5-[((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-methylethyl)oxy]-N-(5-methylpyrazin-2-yl)benzamide

Product 1

HCID 53482140HCID 53482140, compoundYield 37.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1M Hydrochloric acid (5 mL) was added to a solution of 3-{[5-(azetidin-1-ylcarbonyl)pyrazin-2-yl]oxy}-5-[((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-methylethyl)oxy]-N-(5-methylpyrazin-2-yl)benzamide (90 mg, 0.16 mmol) in methanol (5 mL) and the mixture stirred at RT for 1 hour. The methanol was removed in vacuo, the residue adjusted to pH6 and then extracted into ethyl acetate (3×50 mL). The combined organics were washed with brine (50 mL), dried (MgSO4), and reduced in vacuo to give a yellow oil which was chromatographed on silica, eluting with 0-5% methanol in ethyl acetate, to give the desired compound as a white foam (28 mg).

Workup

  1. customThe methanol was removed in vacuo
  2. extractionextracted into ethyl acetate (3×50 mL)
  3. washThe combined organics were washed with brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. customto give a yellow oil which
  6. customwas chromatographed on silica
  7. washeluting with 0-5% methanol in ethyl acetate

Sources & evidence

ORD record
ord-85fae12d762c4e1b8392cc45193638cd
Source dataset
uspto-grants-2010_01
Patent number
US07642259B2

Reaction notes

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