Ammonia → HCID 58513608, compound

HRID 1817889Notes

Reaction equation

HRID 1817889 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:16][CH2:17][CH:18]2[CH2:20][CH2:19]2)=[C:6]([NH:8][C:9](=O)[CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:7]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O.N>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:16]([CH2:17][CH:18]3[CH2:20][CH2:19]3)[C:9]([CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:8][C:6]=2[CH:7]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 59253284HCID 59253284, compound

Product 1

HCID 58513608HCID 58513608, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of N-{5-bromo-2-[(cyclopropylmethyl)amino]phenyl}-3,3-dimethylbutanamide (Step C, 761 mg, 2.24 mmol) and p-toluenesulfonic acid monohydrate (426 mg, 2.24 mmol) in toluene (40 mL) was stirred under reflux for 23 h with Dean-Stark apparatus. Water (10 mL) and aqueous ammonia (5 mL) were added and the mixture was extracted with ethyl acetate (20 mL×2). The organic extracts were dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=9:1 as eluent) to give the title compound (651 mg, 90%) as a brown oil.

Workup

  1. temperatureunder reflux for 23 h with Dean-Stark apparatus
  2. extractionthe mixture was extracted with ethyl acetate (20 mL×2)
  3. dry with materialThe organic extracts were dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=9:1 as eluent)

Sources & evidence

ORD record
ord-d8d20ebcd6b44a49b7020ec676648670
Source dataset
uspto-grants-2009_10
Patent number
US07598393B2

Reaction notes

Loading…