HCID 53629614, compound → 3-{[5-(azetidin-1-ylcarbonyl)pyridin-2-yl]oxy}-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}-N-1,3-thiazol-2-ylbenzamide

HRID 1990115Notes

Reaction equation

HRID 1990115 reaction equation
[N:1]1([C:5]([C:7]2[CH:8]=[CH:9][C:10]([O:13][C:14]3[CH:15]=[C:16]([CH:25]=[C:26]([O:28][C@@H:29]([CH3:39])[CH2:30][O:31][Si](C(C)(C)C)(C)C)[CH:27]=3)[C:17]([NH:19][C:20]3[S:21][CH:22]=[CH:23][N:24]=3)=[O:18])=[N:11][CH:12]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1>CO.Cl>[N:1]1([C:5]([C:7]2[CH:8]=[CH:9][C:10]([O:13][C:14]3[CH:15]=[C:16]([CH:25]=[C:26]([O:28][C@@H:29]([CH3:39])[CH2:30][OH:31])[CH:27]=3)[C:17]([NH:19][C:20]3[S:21][CH:22]=[CH:23][N:24]=3)=[O:18])=[N:11][CH:12]=2)=[O:6])[CH2:2][CH2:3][CH2:4]1

Participants

4

Reactant 1

HCID 53629614HCID 53629614, compound

Product 1

HCID 160400333-{[5-(azetidin-1-ylcarbonyl)pyridin-2-yl]oxy}-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}-N-1,3-thiazol-2-ylbenzamideYield 43.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of 3-{[5-(azetidin-1-ylcarbonyl)pyridin-2-yl]oxy}-5-[((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-methylethyl)oxy]-N-1,3-thiazol-2-ylbenzamide (0.15 g, 0.33 mmol) in methanol (10 mL) and 1M hydrochloric acid (10 mL) was stirred for 90 mins at RT. The volatiles were removed in vacuo and the residue taken to pH6 with saturated aqueous sodium bicarbonate solution then extracted into ethyl acetate (3×30 mL) and the combined organic layers washed with water (30 mL), brine (30 mL), dried (MgSO4), filtered and the solvents removed in vacuo to a residue which was chromatographed on silica eluting with a gradient of 0-10% methanol in ethyl acetate to give the desired compound (65 mg).

Workup

  1. customThe volatiles were removed in vacuo
  2. extractionthen extracted into ethyl acetate (3×30 mL)
  3. washthe combined organic layers washed with water (30 mL), brine (30 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvents removed in vacuo to a residue which
  7. customwas chromatographed on silica eluting with a gradient of 0-10% methanol in ethyl acetate

Sources & evidence

ORD record
ord-fb614f8a14544b4aa67d99baef59ab07
Source dataset
uspto-grants-2010_01
Patent number
US07642259B2

Reaction notes

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