Acetonitrile → HCID 68456140, compound

HRID 2358420Notes

Reaction equation

HRID 2358420 reaction equation
Cl.[NH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][C:4]=1[F:11].C1([O:18][C:19](=O)[NH:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:24][CH:23]=2)C=CC=CC=1.C(#N)C>C(N(CC)CC)C>[NH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH:8][C:19]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:24][CH:23]=2)=[O:18])=[CH:5][C:4]=1[F:11]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 11708154HCID 11708154, compoundHCID 59389711Phenyl [(4-tert-butylphenyl)methyl]carbamate

Product 1

HCID 68456140HCID 68456140, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To the 50 ml of round bottom flask were put 4-amino-3-fluorobenzylamine hydrochloride (0.46 g, 3.28 mmol) and 4-t-butylbenzylcarbamic acid phenyl ester (1.1 eq, 1.02 g). And to this mixture was poured 20 ml acetonitrile and added triethylamine (excess, 0.5 ml) and refluxed 12 hours. After confirming the completion of the reaction with TLC, the reaction mixture was extracted with ethylacetate, washed with 1N HCl solution. And the combined organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The obtained liquid was column-chromatographed (n-hexane/ethyl acetate=1/1).

Workup

  1. customTo the 50 ml of round bottom flask were put
  2. temperaturerefluxed 12 hours
  3. customthe completion of the reaction with TLC
  4. extractionthe reaction mixture was extracted with ethylacetate
  5. washwashed with 1N HCl solution
  6. dry with materialAnd the combined organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained liquid was column-chromatographed (n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-c0ce132ec31b427c8a77426ccd0cc720
Source dataset
uspto-grants-2010_07
Patent number
US07763657B2

Reaction notes

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