HCID 59722730, compound → HCID 59722677, compound

HRID 1664849Notes

Reaction equation

HRID 1664849 reaction equation
[CH3:1][Mg]Br.[F:4][C:5]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:6]=1[C@H:12]1[CH2:18][N:17]2[C:19]([CH:22]=[O:23])=[CH:20][N:21]=[C:16]2[C@H:15]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:14][CH2:13]1>O1CCCC1>[F:4][C:5]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:6]=1[C@H:12]1[CH2:18][N:17]2[C:19]([CH:22]([OH:23])[CH3:1])=[CH:20][N:21]=[C:16]2[C@H:15]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:28])([CH3:30])[CH3:29])[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 59722730HCID 59722730, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 59722677HCID 59722677, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methylmagnesium bromide (3.0 M in ether; 0.33 mL, 1.0 mmol) was added to a solution of tert-butyl (6S,9R)-6-(2,3-difluorophenyl)-3-formyl-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepin-9-ylcarbamate (130 mg, 0.33 mmol) in tetrahydrofuran (3 mL) at 0° C. After 10 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. MS 408.1 (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

Sources & evidence

ORD record
ord-83c8f30787bd42f09aed13f23ea76fd8
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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