HCID 86720685, compound → HCID 71187175, compound

HRID 1844562Notes

Reaction equation

HRID 1844562 reaction equation
[CH2:1]([Mg]Br)[CH3:2].CN(C=[N:9][S:10]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:24]([O:25][CH3:26])=[CH:23][CH:22]=[C:21]([C:27]3[N:31]([CH3:32])[C:30]([C:33](N(OC)C)=[O:34])=[CH:29][C:28]=3[CH3:39])[CH:20]=2)=[CH:15][CH:14]=1)(=[O:12])=[O:11])C>C1COCC1>[CH3:32][N:31]1[C:30]([C:33](=[O:34])[CH2:1][CH3:2])=[CH:29][C:28]([CH3:39])=[C:27]1[C:21]1[CH:22]=[CH:23][C:24]([O:25][CH3:26])=[C:19]([C:16]2[CH:17]=[CH:18][C:13]([S:10]([NH2:9])(=[O:11])=[O:12])=[CH:14][CH:15]=2)[CH:20]=1

Participants

4

Reactant 2

HCID 86720685HCID 86720685, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 71187175HCID 71187175, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

Ethyl magnesium bromide (0.53 g, 3.96 ml, 3.98 mmol) was added drop wise to a solution of 5-(4′-(N-((dimethylamino)methylene)sulfamoyl)-6-methoxy-[1,1′-biphenyl]-3-yl)-N-methoxy-N,1,4-trimethyl-1H-pyrrole-2-carboxamide (Step 5, 0.4 g, 0.80 mmol) in anhydrous THF (10 ml) under stirring at 25° C. The reaction mixture was heated at 70-75° C. for 1 hour. The progress of the reaction was monitored by TLC. The reaction mixture was then cooled to 0° C. and was quenched by addition of saturated solution of ammonium chloride (10 ml). The resulting mixture was extracted with ethyl acetate (3×30 ml). The combined organic layer was dried over anhydrous Na2SO4. The solvent was evaporated from the dried organic layer under reduced pressure to obtain a crude product, which was then purified by column chromatography using mixture of ethyl acetate and hexane as an eluent to obtain the title compound 10 (0.04 g, 12.12%).

Workup

  1. temperatureThe reaction mixture was heated at 70-75° C. for 1 hour
  2. temperatureThe reaction mixture was then cooled to 0° C.
  3. customwas quenched by addition of saturated solution of ammonium chloride (10 ml)
  4. extractionThe resulting mixture was extracted with ethyl acetate (3×30 ml)
  5. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  6. customThe solvent was evaporated from the dried organic layer under reduced pressure
  7. customto obtain a crude product, which
  8. customwas then purified by column chromatography
  9. additionmixture of ethyl acetate and hexane as an eluent
  10. customto obtain the title compound 10 (0.04 g, 12.12%)

Sources & evidence

ORD record
ord-ea175d5d388048309a4a8effdd9abe5c
Source dataset
uspto-grants-2015_02
Patent number
US08946432B2

Reaction notes

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