Hydrochloric Acid → HCID 53629608, compound

HRID 1990263Notes

Reaction equation

HRID 1990263 reaction equation
Cl.[N:2]1([C:6]([C:8]2[N:13]=[CH:12][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])=[CH:10][CH:9]=2)=[O:7])[CH2:5][CH2:4][CH2:3]1>CO>[N:2]1([C:6]([C:8]2[N:13]=[CH:12][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])=[CH:10][CH:9]=2)=[O:7])[CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 536296833-{[6-(azetidin-1-ylcarbonyl)pyridin-3-yl]oxy}-5-[((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-methylethyl)oxy]-N-(5-methylpyrazin-2-yl)benzamide

Product 1

HCID 53629608HCID 53629608, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1M Hydrochloric acid (5 mL) was added to a solution of 3-{[6-(azetidin-1-ylcarbonyl)pyridin-3-yl]oxy}-5-[((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-methylethyl)oxy]-N-(5-methylpyrazin-2-yl)benzamide (82 mg, 0.14 mmol) in methanol (5 mL) and stirred at RT for 1 hour. The methanol was removed in vacuo and the residue taken to pH6, extracted into ethyl acetate (3×50 mL) and the combined organics washed with brine (50 mL), dried (MgSO4), filtered and reduced in vacuo. The crude yellow oil was chromatographed on silica, eluting with 0-5% methanol in ethyl acetate, to give the desired compound as a white foam (36 mg). The compound could be crystallised from a mixture of tert-butylmethyl ether and methanol. 1H NMR δ (CDCl3): 1.24 (d, 3H), 1.81 (s, 1H), 2.28 (quin, 2H), 2.48 (s, 3H), 3.67-3.72 (m, 2H), 4.17 (t, 2H), 4.47-4.54 (m, 1H), 4.63 (t, 2H), 6.73 (t, 1H), 7.09 (t, 1H), 7.25 (t, 1H), 7.27-7.30 (m, 1H), 8.01-8.06 (m, 2H), 8.24 (d, 1H), 8.58 (s, 1H), 9.44 (d, 1H); m/z 464 (M+H)+

Workup

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

Sources & evidence

ORD record
ord-92813ad25689430797211c62ae8f11a4
Source dataset
uspto-grants-2010_01
Patent number
US07642259B2

Reaction notes

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