Ethylene Glycol → HCID 59722543, compound

HRID 1664863Notes

Reaction equation

HRID 1664863 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]C)([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.[CH2:37](O)[CH2:38][OH:39]>>[NH2:29][C@@H:17]1[CH2:16][CH2:15][C@@H:14]([C:8]2[C:9]([F:13])=[CH:10][CH:11]=[CH:12][C:7]=2[F:6])[CH2:20][N:19]2[C:21]([C:24]([CH3:25])([O:27][CH2:37][CH2:38][OH:39])[CH3:26])=[CH:22][N:23]=[C:18]12

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 6395Methanesulfonic AcidHCID 86620133HCID 86620133, compound

Product 1

HCID 59722543HCID 59722543, compound

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) and the mixture heated to 60° C. After 18 h, the reaction mixture was concentrated. Saturated aqueous sodium bicarbonate was added and the mixture was extracted with dichloromethane (3×), and the combined organic extracts were washed with saturated brine, dried over sodium sulfate, filtered and concentrated. MS 366.1 (M+1).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additionSaturated aqueous sodium bicarbonate was added
  3. extractionthe mixture was extracted with dichloromethane (3×)
  4. washthe combined organic extracts were washed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6de7ac219a2040098175b3420931e55e
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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