Hydrochloric Acid → 3-[4-(azetidin-1-ylcarbonyl)phenoxy]-n-(1,5-dimethyl-1h-pyrazol-3-yl)-5-[(1S)-2-hydroxy-1-methylethoxy]benzamide

HRID 20607Notes

Reaction equation

HRID 20607 reaction equation
Cl.[N:2]1([C:6]([C:8]2[CH:42]=[CH:41][C:11]([O:12][C:13]3[CH:14]=[C:15]([CH:26]=[C:27]([O:29][C@@H:30]([CH3:40])[CH2:31][O:32][Si](C(C)(C)C)(C)C)[CH:28]=3)[C:16]([NH:18][C:19]3[CH:23]=[C:22]([CH3:24])[N:21]([CH3:25])[N:20]=3)=[O:17])=[CH:10][CH:9]=2)=[O:7])[CH2:5][CH2:4][CH2:3]1.C(=O)(O)[O-].[Na+]>CO.C(OCC)(=O)C>[N:2]1([C:6]([C:8]2[CH:42]=[CH:41][C:11]([O:12][C:13]3[CH:14]=[C:15]([CH:26]=[C:27]([O:29][C@@H:30]([CH3:40])[CH2:31][OH:32])[CH:28]=3)[C:16]([NH:18][C:19]3[CH:23]=[C:22]([CH3:24])[N:21]([CH3:25])[N:20]=3)=[O:17])=[CH:10][CH:9]=2)=[O:7])[CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 593469243-[4-(azetidin-1-ylcarbonyl)phenoxy]-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-n-(1,5-dimethyl-1h-pyrazol-3-yl)benzamide

Product 1

HCID 116983743-[4-(azetidin-1-ylcarbonyl)phenoxy]-n-(1,5-dimethyl-1h-pyrazol-3-yl)-5-[(1S)-2-hydroxy-1-methylethoxy]benzamideYield 66.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

3.5M Hydrochloric acid (1.0 mL) was added to a solution of 3-[4-(azetidin-1-ylcarbonyl)phenoxy]-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-N-(1,5-dimethyl-1H-pyrazol-3-yl)benzamide (232 mg, 0.4 mmol) in methanol (10 mL). The reaction mixture was stirred for 45 minutes then saturated sodium bicarbonate added until the pH was adjusted to 7. The mixture was reduced in vacuo. The residue was dissolved in ethyl acetate (50 mL), washed water (25 mL) and brine (25 mL). Dried (MgSO4) and reduced to a white foam. The crude product was purified by chromatography on silica, eluting with 0-10% methanol in ethyl acetate, to obtain the required product as a white foam (123 mg).

Workup

  1. washwashed water (25 mL) and brine (25 mL)
  2. dry with materialDried (MgSO4)
  3. customThe crude product was purified by chromatography on silica
  4. washeluting with 0-10% methanol in ethyl acetate

Sources & evidence

ORD record
ord-0592ca20aa014d2dbdd37db8f75f5258
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Reaction notes

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