HCID 59722591, compound → HCID 59722729, compound

HRID 1664842Notes

Reaction equation

HRID 1664842 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]([CH2:22][CH:23]=[O:24])=[CH:20][N:21]=[C:16]2[C@H:15]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[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]([CH2:22][CH:23]([OH:24])[CH3:1])=[CH:20][N:21]=[C:16]2[C@H:15]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:29])([CH3:31])[CH3:30])[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 59722591HCID 59722591, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 59722729HCID 59722729, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methylmagnesium bromide (3.0 M in ether; 0.70 mL, 2.10 mmol) was added to a solution of tert-butyl (6S,9R)-6-(2,3-difluorophenyl)-3-(2-oxoethyl)-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepin-9-ylcarbamate (85 mg, 0.210 mmol) in tetrahydrofuran (5 mL). After 2 h, the reaction was quenched with saturated aqueous ammonium chloride. Saturated aqueous sodium bicarbonate was added and the mixture was extracted with dichloromethane (3×). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. Purification by silica gel chromatography (100% dichloromethane→95% dichloromethane/methanol) gave the title compound (73 mg). MS 422.2 (M+1).

Workup

  1. customthe reaction was quenched with saturated aqueous ammonium chloride
  2. additionSaturated aqueous sodium bicarbonate was added
  3. extractionthe mixture was extracted with dichloromethane (3×)
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography (100% dichloromethane→95% dichloromethane/methanol)

Sources & evidence

ORD record
ord-2642321c83fd49b3b37254e1f713d24f
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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