Acetonitrile → HCID 67242347, compound

HRID 2423357Notes

Reaction equation

HRID 2423357 reaction equation
Cl.[F:2][C:3]1[CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[C:8]([F:15])=CC=1CN.C1(O[C:23](=[O:36])[NH:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:28][CH:27]=2)C=CC=CC=1.[C:37](#[N:39])C.C([N:42]([CH2:45][CH3:46])CC)C>>[C:32]([C:29]1[CH:28]=[CH:27][C:26]([CH2:25][NH:24][C:23](=[O:36])[NH:39][CH2:37][C:9]2([S:11]([CH3:14])(=[O:12])=[O:13])[C:8]([F:15])=[CH:46][C:45]([NH:42][S:11]([CH3:9])(=[O:13])=[O:12])=[C:3]([F:2])[CH2:10]2)=[CH:31][CH:30]=1)([CH3:33])([CH3:34])[CH3:35]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 59389711Phenyl [(4-tert-butylphenyl)methyl]carbamateHCID 67243746HCID 67243746, compound

Product 1

HCID 67242347HCID 67242347, compound

Procedure

2,5-difluoro-4-methanesulfonylbenzylamine hydrochloride (70 mg, 0.26 mmol) and 4-t-butylbenzylcarbamic acid phenyl ester (1.1 eq, 80 mg) were put into the 25 ml one-neck round bottom flask and poured with 15 ml acetonitrile. To this solution was added triethylamine (excess, 0.5 ml) and stirred for 18 hours. After confirming the completion of the reaction with TLC, the reaction solution was concentrated under reduced pressure. The obtained substance was extracted with methylene chloride and washed with 1M HCl solution, dried over MgSO4, filtered and concentrated under reduced pressure. The obtained liquid was column-chromatographed (n-hexane/ethyl acetate=2/3) to yield title compound (64 mg)

Workup

  1. customthe completion of the reaction with TLC
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. extractionThe obtained substance was extracted with methylene chloride
  4. washwashed with 1M HCl solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained liquid was column-chromatographed (n-hexane/ethyl acetate=2/3)

Sources & evidence

ORD record
ord-aa67f452ada24d96bc2c6267226f3c87
Source dataset
uspto-grants-2011_06
Patent number
US07960584B2

Reaction notes

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