Hydrochloric Acid → HCID 66937474, compound

HRID 1521375Notes

Reaction equation

HRID 1521375 reaction equation
Cl[C:2]1[N:6](COCCOC)[C:5]2[CH:13]=[C:14]([Cl:24])[C:15]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:16][C:4]=2[N:3]=1.[NH:25]1[CH:29]=[C:28]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:27]=[N:26]1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CN(C=O)C>[CH2:33]([O:32][C:30]([C:28]1[CH:29]=[N:25][N:26]([C:2]2[NH:6][C:5]3[CH:13]=[C:14]([Cl:24])[C:15]([O:17][C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)=[CH:16][C:4]=3[N:3]=2)[CH:27]=1)=[O:31])[CH3:34]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 142179ethyl 1H-pyrazole-4-carboxylateHCID 66937209HCID 66937209, compound

Product 1

HCID 66937474HCID 66937474, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 2,6-dichloro-1-(2-methoxy-ethoxymethyl)-5-phenoxy-1H-benzoimidazole (0.251 g, 0.684 mmol) and ethyl pyrazole-4-carboxylate (0.115 g, 0.820 mmol) in dry DMF (4 mL) was added anhydrous cesium carbonate (0.535 g, 1.64 mmol). The stirred suspension was heated in 80° C. bath in a sealed tube for 2 h. After coming to ambient temperature, the reaction mixture was added to ice water (100 mL), acidified with 1N HCl (3 mL) and extracted with dichloromethane. The combined organic layers were washed with water, brine, dried, filtered, and concentrated under reduced pressure to afford the titled product as a crude orange paste (0.361 g). MS (ESI/CI): mass calcd. for C23H23ClN4O5, 470; m/z found, 471 [M+H]+.

Workup

  1. customAfter coming to ambient temperature
  2. extractionextracted with dichloromethane
  3. washThe combined organic layers were washed with water, brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-817aaa0476d44533a1579e49b882fb11
Source dataset
uspto-grants-2015_07
Patent number
US09073923B2

Reaction notes

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