Cesium carbonate → HCID 178462520, compound

HRID 1823773Notes

Reaction equation

HRID 1823773 reaction equation
[CH:1]1([C:4]([NH:6][C:7]2[NH:11][C:10]3[CH:12]=[CH:13][C:14]([O:16][S:17]([C:20]4[CH:25]=[CH:24][C:23](F)=[CH:22][CH:21]=4)(=[O:19])=[O:18])=[CH:15][C:9]=3[N:8]=2)=[O:5])[CH2:3][CH2:2]1.[NH2:27][CH2:28][CH:29]1[CH2:33][CH2:32][CH2:31][N:30]1[CH2:34][CH3:35].C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[CH:1]1([C:4]([NH:6][C:7]2[NH:11][C:10]3[CH:12]=[CH:13][C:14]([O:16][S:17]([C:20]4[CH:25]=[CH:24][C:23]([NH:27][CH2:28][CH:29]5[CH2:33][CH2:32][CH2:31][N:30]5[CH2:34][CH3:35])=[CH:22][CH:21]=4)(=[O:19])=[O:18])=[CH:15][C:9]=3[N:8]=2)=[O:5])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 178522509HCID 178522509, compound

Product 1

HCID 178462520HCID 178462520, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

Title compound was obtained by reacting 12 mg of 4-fluoro-benzenesulfonic acid 2-(cyclopropanecarbonyl-amino)-1H-benzoimidazol-5-yl ester (example 55) with 21 mg of 2-(aminomethyl)-1-ethylpyrrolidine and 50 mg cesium carbonate in 600 μl dimethylsulfoxide. Reaction was performed in a 24 well Inox plate for high pressure. The reaction mixture was put under 10 bars argon pressure and then heated to 110° C. for 50 hours. Cesium carbonate was filtered off and compound in DMSO was directly purified by LCMS triggered purification yielding 10.7 mg title compound. (LC/MS analysis: retention time=2.58 min, mass spectrum: 483.99, [M+H]+.

Workup

  1. customReaction
  2. filtrationCesium carbonate was filtered off
  3. customcompound in DMSO was directly purified by LCMS
  4. custompurification

Sources & evidence

ORD record
ord-384cc36c70834df89fd03931d29773a7
Source dataset
uspto-grants-2006_05
Patent number
US07041668B2

Reaction notes

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