HCID 59722739, compound → HCID 59722606, compound

HRID 1664854Notes

Reaction equation

HRID 1664854 reaction equation
[CH3:1][Mg]Br.[C:4]([C:7]1[N:11]2[CH2:12][C@H:13]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[C:26]=3[F:32])[CH2:14][CH2:15][C@@H:16]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C:10]2=[N:9][CH:8]=1)(=[O:6])[CH3:5]>O1CCCC1>[F:32][C:26]1[C:27]([F:31])=[CH:28][CH:29]=[CH:30][C:25]=1[C@H:13]1[CH2:12][N:11]2[C:7]([C:4]([OH:6])([CH3:1])[CH3:5])=[CH:8][N:9]=[C:10]2[C@H:16]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 59722739HCID 59722739, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 59722606HCID 59722606, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methylmagnesium bromide (3.0 M in ether; 90 μL, 0.27 mmol) was added to a solution of tert-butyl (6S,9R)-3-acetyl-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepin-9-ylcarbamate (22 mg, 0.05 mmol) in tetrahydrofuran (1 mL) at 0° C., and the reaction mixture was allowed to warm to ambient temperature. After 30 min, the reaction was quenched with water and the mixture was extracted with dichloromethane (3×). The organic layer was washed with water, saturated brine, dried over magnesium sulfate, filtered and concentrated. Purification by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (15 mg). MS 422.2 (M+1).

Workup

  1. customthe reaction was quenched with water
  2. extractionthe mixture was extracted with dichloromethane (3×)
  3. washThe organic layer was washed with water, saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-9430af1994304c8ba64c74b3c236cad3
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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