Tetrahydrofuran → HCID 66924319, compound

HRID 1360202Notes

Reaction equation

HRID 1360202 reaction equation
ClC(Cl)(Cl)[C:3]1[O:7][N:6]=[C:5]([C:8]2[C:9]([NH:17][CH:18]3[CH:25]4[CH2:26][C:21]5([OH:28])[CH2:22][CH:23]([CH2:27][CH:19]3[CH2:20]5)[CH2:24]4)=[C:10]3[CH:16]=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)[N:4]=1.[CH2:31]([NH2:33])[CH3:32].CO.C(OCC)(=O)C.O1CCCC1>CN1CCCC1=O.O>[CH2:31]([NH:33][C:3]1[O:7][N:6]=[C:5]([C:8]2[C:9]([NH:17][CH:18]3[CH:19]4[CH2:20][C:21]5([OH:28])[CH2:22][CH:23]([CH2:24][CH:25]3[CH2:26]5)[CH2:27]4)=[C:10]3[CH:16]=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)[N:4]=1)[CH3:32]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 66924168HCID 66924168, compoundHCID 86635283HCID 86635283, compound

Product 1

HCID 66924319HCID 66924319, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 4-({5-[5-(trichloromethyl)-1,2,4-oxadiazole-3-yl]-1H-pyrrolo[2,3-b]pyridine-4-yl}amino) adamantan-1-ol (80 mg) in 1-methyl-2-pyrrolidinone (1.6 ml) was added ethylamine/methanol solution (2.0M) (1.7 ml) under ice cooling. The reaction solution was stirred for 5 hours under ambient temperature. To the reaction solution were added ethyl acetate, tetrahydrofuran, and water. The mixture was extracted with a mixture solvent of tetrahydrofuran and ethyl acetate, and washed with saturated brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel (NH silica gel) column chromatography (chloroform:methanol=100:0 to 91:9) to obtain 4-({5-[5-(ethylamino)-1,2,4-oxadiazole-3-yl]-1H -pyrrolo[2,3-b]pyridine-4-yl}amino)adamantan-1-ol (50 mg) as a yellow solid.

Workup

  1. extractionThe mixture was extracted with a mixture solvent of tetrahydrofuran and ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel (NH silica gel) column chromatography (chloroform:methanol=100:0 to 91:9)

Sources & evidence

ORD record
ord-d4a9395292e74f5c8cf20267b1527566
Source dataset
uspto-grants-2011_02
Patent number
US07879844B2

Reaction notes

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