HCID 86720683, compound → HCID 71203605, compound

HRID 1844556Notes

Reaction equation

HRID 1844556 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[S:31][C:30]([C:32](N(OC)C)=[O:33])=[C:29]([CH3:38])[C:28]=3[CH3:39])[CH:20]=2)=[CH:15][CH:14]=1)(=[O:12])=[O:11])C>C1COCC1>[CH3:39][C:28]1[C:29]([CH3:38])=[C:30]([C:32](=[O:33])[CH2:1][CH3:2])[S:31][C:27]=1[C:21]1[CH:22]=[CH:23][C:24]([O:25][CH3:26])=[C:19]([C:16]2[CH:15]=[CH:14][C:13]([S:10]([NH2:9])(=[O:12])=[O:11])=[CH:18][CH:17]=2)[CH:20]=1

Participants

4

Reactant 2

HCID 86720683HCID 86720683, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 71203605HCID 71203605, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
72.5 °C

Procedure

Ethyl magnesium bromide (0.14 g, 1.1 ml, 1.06 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,3,4-trimethylthiophene-2-carboxamide (Step 7, 0.11 g, 0.21 mmol) in anhydrous THF (10 ml) at 25° C. under stirring. The reaction mixture was then heated to 70-75° C. for 1 hour. The progress of the reaction was monitored by TLC. The reaction mixture was then cooled to 0° C. The cooled reaction mixture was then quenched with a saturated solution of ammonium chloride (10 ml). The resultant mixture was then extracted with ethyl acetate (3×20 ml). The combined organic layer was dried over anhydrous Na2SO4. The solvent was evaporated from the organic layer under reduced pressure to obtain a crude product, which was then purified by column chromatography using 35% ethyl acetate in hexane as an eluent to obtain the title compound 9 (0.03 g, 33.0%).

Workup

  1. temperatureThe reaction mixture was then cooled to 0° C
  2. customThe cooled reaction mixture
  3. customwas then quenched with a saturated solution of ammonium chloride (10 ml)
  4. extractionThe resultant mixture was then extracted with ethyl acetate (3×20 ml)
  5. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  6. customThe solvent was evaporated from the organic layer under reduced pressure
  7. customto obtain a crude product, which
  8. customwas then purified by column chromatography
  9. customto obtain the title compound 9 (0.03 g, 33.0%)

Sources & evidence

ORD record
ord-318233cf4c3f4b77bb1cf93c829b64f5
Source dataset
uspto-grants-2015_02
Patent number
US08946432B2

Reaction notes

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