Hydrochloric Acid → HCID 16039688, compound

HRID 1990185Notes

Reaction equation

HRID 1990185 reaction equation
[N:1]1([C:5]([C:7]2[CH:8]=[C:9]([Cl:43])[C:10]([O:13][C:14]3[CH:15]=[C:16]([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:17]([NH:19][C:20]3[CH:24]=[CH:23][N:22]([CH:25]([CH3:27])[CH3:26])[N:21]=3)=[O:18])=[N:11][CH:12]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.Cl.C(=O)(O)[O-].[Na+]>CO>[N:1]1([C:5]([C:7]2[CH:8]=[C:9]([Cl:43])[C:10]([O:13][C:14]3[CH:15]=[C:16]([CH:28]=[C:29]([O:31][C@@H:32]([CH3:42])[CH2:33][OH:34])[CH:30]=3)[C:17]([NH:19][C:20]3[CH:24]=[CH:23][N:22]([CH:25]([CH3:27])[CH3:26])[N:21]=3)=[O:18])=[N:11][CH:12]=2)=[O:6])[CH2:2][CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 536296473-{[5-(Azetidin-1-ylcarbonyl)-3-chloropyridin-2-yl]oxy}-5-[((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-methylethyl)oxy]-N-[1-(1-methylethyl)-1H-pyrazol-3-yl]benzamide

Product 1

HCID 16039688HCID 16039688, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-{[5-(Azetidin-1-ylcarbonyl)-3-chloropyridin-2-yl]oxy}-5-[((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-methylethyl)oxy]-N-[1-(1-methylethyl)-1H-pyrazol-3-yl]benzamide (142 mg, 0.23 mmol) in methanol (2 mL) was stirred with 3.5M hydrochloric acid (0.2 mL, 0.68 mmol) for 1 hour. The solution was neutralised with saturated sodium bicarbonate solution and the organic solvent was removed under reduced pressure. The residue was extracted with ethyl acetate (3×10 mL), dried (MgSO4), filtered and the solvent removed under reduced pressure. The residue was purified by chromatography on silica, eluting with 75-100% ethyl acetate in hexane, to give the required product as a white foam (99 mg).

Workup

  1. customthe organic solvent was removed under reduced pressure
  2. extractionThe residue was extracted with ethyl acetate (3×10 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customThe residue was purified by chromatography on silica
  7. washeluting with 75-100% ethyl acetate in hexane

Sources & evidence

ORD record
ord-390a394b657a4817879934f8fb3282fb
Source dataset
uspto-grants-2010_01
Patent number
US07642259B2

Reaction notes

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