Water → HCID 23600251, compound

HRID 892106Notes

Reaction equation

HRID 892106 reaction equation
[CH2:1]([N:8]1[C:16]2[C:15]3=[N:17][C@H:18]([CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:19][N:14]3[C:13](=[O:27])[N:12]([CH2:28][CH2:29][CH3:30])[C:11]=2[N:10]=[C:9]1Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[NH:38]1[CH2:42][CH2:41][CH2:40][CH2:39]1.O>CN(C)C=O>[CH2:1]([N:8]1[C:16]2[C:15]3=[N:17][C@H:18]([CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:19][N:14]3[C:13](=[O:27])[N:12]([CH2:28][CH2:29][CH3:30])[C:11]=2[N:10]=[C:9]1[N:38]1[CH2:42][CH2:41][CH2:40][CH2:39]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 69661588HCID 69661588, compound

Product 1

HCID 23600251HCID 23600251, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Compound 35 (500 mg, 1.05 mmol) obtained in Example 35 was dissolved in N,N-dimethylformamide (15 mL), to the solution were added potassium carbonate (430 mg, 3.11 mmol, 3.0 equivalents) and pyrrolidine (260 μL, 3.11 mmol, 3.0 equivalents), and then the mixture was stirred with heating at 100° C. for 3.5 hours. To the reaction solution was added water, the mixture was extracted with ethyl acetate, and the extract was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (chloroform:methanol=99:1 to 97:3), and to the residue were added acetone and diethyl ether. The deposited crystals were collected by filtration to obtain the title compound (467 mg, 95%) as white crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washthe extract was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (chloroform:methanol=99:1 to 97:3)
  6. additionto the residue were added acetone and diethyl ether
  7. filtrationThe deposited crystals were collected by filtration

Sources & evidence

ORD record
ord-8bbd7ddd8d70404e97c4146aaa974229
Source dataset
uspto-grants-2006_02
Patent number
US07005430B2

Reaction notes

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