Cesium carbonate → HCID 16040146, compound

HRID 1989907Notes

Reaction equation

HRID 1989907 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[OH:7][C:8]1[CH:9]=[C:10]([CH:20]=[C:21]([O:23][CH:24]([CH3:26])[CH3:25])[CH:22]=1)[C:11]([NH:13][C:14]1[CH:18]=[CH:17][N:16]([CH3:19])[N:15]=1)=[O:12].[N:27]1([C:31]([C:33]2[S:37][C:36](Cl)=[N:35][CH:34]=2)=[O:32])[CH2:30][CH2:29][CH2:28]1>C(#N)C>[N:27]1([C:31]([C:33]2[S:37][C:36]([O:7][C:8]3[CH:9]=[C:10]([CH:20]=[C:21]([O:23][CH:24]([CH3:26])[CH3:25])[CH:22]=3)[C:11]([NH:13][C:14]3[CH:18]=[CH:17][N:16]([CH3:19])[N:15]=3)=[O:12])=[N:35][CH:34]=2)=[O:32])[CH2:28][CH2:29][CH2:30]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 53629630Azetidin-1-yl(2-chlorothiazol-5-yl)methanoneHCID 591271833-hydroxy-5-isopropoxy-N-(1-methyl-1H-pyrazol-3-yl)benzamide

Product 1

HCID 16040146HCID 16040146, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Cesium carbonate (488 mg, 1.5 mmol) was added to a solution of 3-hydroxy-5-[(1-methylethyl)oxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide (187 mg, 0.5 mmol) and 5-(azetidin-1-ylcarbonyl)-2-chloro-1,3-thiazole (152 mg, 0.75 mmol) in acetonitrile (5 mL) and the stirred mixture heated at 160° in a Biotage Initiator Microwave for 2 hours. The mixture was cooled to RT and pressure, poured onto water (75 mL) then extracted with ethyl acetate (3×25 mL). The combined organic layers were washed with brine, dried (MgSO4) and evaporated to a residue which was chromatographed on silica eluting with ethyl acetate, to give the desired compound (142 mg). 1H NMR δ (CDCl3): 1.3 (d, 6H), 2.4 (m, 2H), 3.7 (s, 3H), 4.1-4.4 (m, 4H), 4.5 (m, 1H), 6.75 (s, 1H), 6.9 (s, 1H), 7.2 (s, 1H), 7.25 (d, 1H), 7.4 (s, 1H) and 8.95 (s, 1H). m/z 442 (M+H)+.

Workup

  1. temperaturethe stirred mixture heated at 160° in a Biotage Initiator Microwave for 2 hours
  2. additionpressure, poured onto water (75 mL)
  3. extractionthen extracted with ethyl acetate (3×25 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated to a residue which
  7. customwas chromatographed on silica eluting with ethyl acetate

Sources & evidence

ORD record
ord-327b93edaafa4fcf9285ef84d5194409
Source dataset
uspto-grants-2010_01
Patent number
US07642263B2

Reaction notes

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