HCID 59722730, compound → HCID 59722707, compound

HRID 1664850Notes

Reaction equation

HRID 1664850 reaction equation
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.[F:6][C:7]1[C:12]([F:13])=[CH:11][CH:10]=[CH:9][C:8]=1[C@H:14]1[CH2:20][N:19]2[C:21]([CH:24]=[O:25])=[CH:22][N:23]=[C:18]2[C@H:17]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:16][CH2:15]1>O1CCCC1>[CH:1]1([CH:24]([OH:25])[C:21]2[N:19]3[CH2:20][C@H:14]([C:8]4[CH:9]=[CH:10][CH:11]=[C:12]([F:13])[C:7]=4[F:6])[CH2:15][CH2:16][C@@H:17]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[C:18]3=[N:23][CH:22]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 59722730HCID 59722730, compoundHCID 178418630HCID 178418630, compound

Product 1

HCID 59722707HCID 59722707, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cyclopropylmagnesium bromide (0.5 M in tetrahydrofuran; 1.53 mL, 0.77 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 (60 mg, 0.15 mmol) in tetrahydrofuran (1 mL) at 0° C. 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. MS 434.2 (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

Sources & evidence

ORD record
ord-eeb9eae167d84ae193969f3187dc4f27
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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