Methanesulfonic Acid → HCID 59722543, compound

HRID 1664917Notes

Reaction equation

HRID 1664917 reaction equation
CS(O)(=O)=O.[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:8]=1[C@H:14]1[CH2:20][N:19]2[C:21]([C:24]([O:27][CH3:28])([CH3:26])[CH3:25])=[CH:22][N:23]=[C:18]2[C@H:17]([NH:29]C(=O)OC(C)(C)C)[CH2:16][CH2:15]1.[C:37](=[O:40])(O)[O-].[Na+]>C(O)CO>[NH2:29][C@@H:17]1[CH2:16][CH2:15][C@@H:14]([C:8]2[C:7]([F:6])=[CH:12][CH:11]=[CH:10][C:9]=2[F:13])[CH2:20][N:19]2[C:21]([C:24]([CH3:26])([O:27][CH2:28][CH2:37][OH:40])[CH3:25])=[CH:22][N:23]=[C:18]12

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 516892Sodium BicarbonateHCID 86620133HCID 86620133, compound

Product 1

HCID 59722543HCID 59722543, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
60 °C

Procedure

Methanesulfonic acid (78 μL, 1.19 mmol) was added to a solution of tert-butyl [(6S,9R)-6-(2,6-difluorophenyl)-3-(1-methoxy-1-methylethyl)-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepin-9-yl]carbamate (104 mg, 0.24 mmol) in ethylene glycol (4 mL). The reaction mixture was heated to 60° C. After 18 h, the mixture was allowed to cool to ambient temperature and saturated aqueous sodium bicarbonate was added. The mixture was extracted with dichloromethane (3×). The organic extracts were washed with saturated aqueous sodium bicarbonate, saturated brine, dried over magnesium sulfate, filtered and concentrated to give the title compound. MS 366.1 (M+1).

Workup

  1. temperatureto cool to ambient temperature
  2. extractionThe mixture was extracted with dichloromethane (3×)
  3. washThe organic extracts were washed with saturated aqueous sodium bicarbonate, saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b36f0464ceb5493c97c8b4a0f31d785a
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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