HCID 86597138, compound → HCID 86597140, compound

HRID 2373797Notes

Reaction equation

HRID 2373797 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C@@H:16]([NH:23][C:24]([C:26]3[CH:27]=[C:28]([C:34]4[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][CH:35]=4)[CH:29]=[CH:30][C:31]=3[O:32][CH3:33])=[O:25])[C:17](=[O:22])N(OC)C)=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].[CH3:44][Mg]Br>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C@@H:16]([NH:23][C:24]([C:26]3[CH:27]=[C:28]([C:34]4[CH:35]=[CH:36][C:37]([C:40]([F:41])([F:42])[F:43])=[CH:38][CH:39]=4)[CH:29]=[CH:30][C:31]=3[O:32][CH3:33])=[O:25])[C:17](=[O:22])[CH3:44])=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 86597138HCID 86597138, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 86597140HCID 86597140, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-Methoxy-4′-trifluoromethyl-biphenyl-3-carboxylic acid [2-(3′-chloro-4′-fluoro-biphenyl-4-yl)-1-(R)-(methoxy-methyl-carbamoyl)-ethyl]-amide (0.1 g, 0.162 mmol) in anhydrous THF (2 mL) was added methyl magnesium bromide [0.35 ml, 1.4M solution in Toluene/THF (75:25)] at 0° C. and allowed to come to room temperature and stirred for 6 h. Reaction was quenched with aq NH4Cl and extracted with EtOAc. Organic layer was washed with water, brine and dried over Na2SO4. Solvent was removed under reduced pressure and the residue was purified by silicagel column chromatography to get pure 4-Methoxy-4′-trifluoromethyl-biphenyl-3-carboxylic acid [1-(R)-(3′-chloro-4′-fluoro-biphenyl-4-ylmethyl)-2-oxo-propyl]-amide (0.055 g)

Workup

  1. customto come to room temperature
  2. customReaction
  3. customwas quenched with aq NH4Cl
  4. extractionextracted with EtOAc
  5. washOrganic layer was washed with water, brine
  6. dry with materialdried over Na2SO4
  7. customSolvent was removed under reduced pressure
  8. customthe residue was purified by silicagel column chromatography

Sources & evidence

ORD record
ord-381b8b73f15c409882facecd4c90bd24
Source dataset
uspto-grants-2008_12
Patent number
US07459472B2

Reaction notes

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