Potassium Carbonate → HCID 53629614, compound

HRID 1011663Notes

Reaction equation

HRID 1011663 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][C:8]([Si:11]([CH3:33])([CH3:32])[O:12][CH2:13][C@@H:14]([O:16][C:17]1[CH:18]=[C:19]([CH:28]=[C:29]([OH:31])[CH:30]=1)[C:20]([NH:22][C:23]1[S:24][CH:25]=[CH:26][N:27]=1)=[O:21])[CH3:15])([CH3:10])[CH3:9].[N:34]1([C:38]([C:40]2[CH:41]=[CH:42][C:43](Cl)=[N:44][CH:45]=2)=[O:39])[CH2:37][CH2:36][CH2:35]1>C(#N)C>[N:34]1([C:38]([C:40]2[CH:41]=[CH:42][C:43]([O:31][C:29]3[CH:28]=[C:19]([CH:18]=[C:17]([O:16][C@@H:14]([CH3:15])[CH2:13][O:12][Si:11]([C:8]([CH3:9])([CH3:10])[CH3:7])([CH3:33])[CH3:32])[CH:30]=3)[C:20]([NH:22][C:23]3[S:24][CH:25]=[CH:26][N:27]=3)=[O:21])=[N:44][CH:45]=2)=[O:39])[CH2:37][CH2:36][CH2:35]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 536296155-(Azetidin-1-ylcarbonyl)-2-chloropyridineHCID 59127134HCID 59127134, compound

Product 1

HCID 53629614HCID 53629614, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
160 °C

Procedure

Potassium carbonate (0.14 g, 0.98 mmol) was added to a mixture of 3-[((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-methylethyl)oxy]-5-hydroxy-N-1,3-thiazol-2-ylbenzamide (200 mg, 0.49 mmol) and 5-(azetidin-1-ylcarbonyl)-2-chloropyridine (96 mg, 0.49 mmol) in acetonitrile (5.0 mL) and the stirred mixture heated at 160° C. in a ‘Biotage initiator Microwave’ for 4 hours. The mixture was allowed to reach RT and pressure and was partitioned between ethyl acetate (50 mL) and water (50 mL). The ethyl acetate layer was separated, washed with water (5×50 mL), brine (50 mL), dried (MgSO4) and evaporated to a residue which was chromatographed on silica, eluting with a gradient of 60-100% ethyl acetate in isohexane, to give the desired compound. (0.15 g).

Workup

  1. customto reach RT
  2. custompressure and was partitioned between ethyl acetate (50 mL) and water (50 mL)
  3. customThe ethyl acetate layer was separated
  4. washwashed with water (5×50 mL), brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. customevaporated to a residue which
  7. customwas chromatographed on silica
  8. washeluting with a gradient of 60-100% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-a07d4cb9899f4ed7b1153a2e58a33936
Source dataset
uspto-grants-2011_07
Patent number
US07977328B2

Reaction notes

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