Water → HCID 22249795, compound

HRID 966034Notes

Reaction equation

HRID 966034 reaction equation
[Br:1]Br.[O:3]1[C:7]([C:8]2[C:9]([CH3:26])=[N:10][N:11]3[C:16]4[N:17]([CH:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[CH2:18][CH2:19][C:15]=4[C:14]([CH3:25])=[N:13][C:12]=23)=[CH:6][C:5]2[CH:27]=[CH:28][CH:29]=[CH:30][C:4]1=2.O>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:6]1[C:5]2[CH:27]=[CH:28][CH:29]=[CH:30][C:4]=2[O:3][C:7]=1[C:8]1[C:9]([CH3:26])=[N:10][N:11]2[C:16]3[N:17]([CH:20]([CH2:21][CH3:22])[CH2:23][CH3:24])[CH2:18][CH2:19][C:15]=3[C:14]([CH3:25])=[N:13][C:12]=12

Participants

6

Reactant 3

HCID 962WaterHCID 24408BromineHCID 22249918HCID 22249918, compound

Product 1

HCID 22249795HCID 22249795, compoundYield 96.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Bromine (1.0 M solution in carbon tetrachloride 0.3 mL, 0.30 mmol) was added to a solution of 3-benzo[b]furan-2-yl-8-(1-ethylpropyl)-2,5-dimethyl-7,8-dihydro-6H-pyrazolo[1,5-a]pyrrolo[3,2-e]pyrimidine (50 mg, 0.13 mmol) in N,N-dimethylformamide (0.3 mL) at 0° C., followed by stirring for one hour. Hypo water was added thereto, and the mixture was diluted with ethyl acetate, washed with an aqueous saturated solution of ammonium chloride and brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (10% ethyl acetate/hexane), to give the title compound (57 mg) as white crystals.

Workup

  1. washwashed with an aqueous saturated solution of ammonium chloride and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customevaporated
  4. customThe residue was purified by silica gel column chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8a19a511e5e84a68907b56a7efb24184
Source dataset
uspto-grants-2005_10
Patent number
US06951865B2

Reaction notes

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