Methanol → 6-Methoxy-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-ol

HRID 8268

Reaction equation

HRID 8268 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([C:19]3[C:23]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=4)=[N:22][N:21]4[CH2:30][CH2:31][CH2:32][C:20]=34)=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:33][CH3:34])C1C=CC=CC=1.C1CC=CCC=1.CO>[Pd].C(O)C>[CH3:34][O:33][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:9]=1[OH:8])[N:16]=[CH:15][CH:14]=[C:13]2[C:19]1[C:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)=[N:22][N:21]2[CH2:30][CH2:31][CH2:32][C:20]=12

Participants

6

Reactant 3

HCID 887MethanolHCID 123431,4-CyclohexadieneHCID 219928767-benzyloxy-6-methoxy-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline

Product 1

HCID 1355323856-Methoxy-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a mixture of 7-benzyloxy-6-methoxy-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline (17 mg, 0.04 mmol) and 10% palladium on activated carbon (3 mg) in absolute ethanol (2 mL) is added 1,4-cyclohexadiene (100 mg, 1.2 mmol). The mixture is stirred at room temperature for 3 h, treated with methanol (500 μL), and heated at 60° C. for 3 h. The mixture is cooled, filtered, and loaded onto an SCX column. The column is washed with water, methanol, and 7 N ammonia in methanol. The appropriate fraction is concentrated in vacuo to yield the title compound, 10 mg (77%), as a yellow solid.

Workup

  1. temperatureheated at 60° C. for 3 h
  2. temperatureThe mixture is cooled
  3. filtrationfiltered
  4. washThe column is washed with water, methanol, and 7 N ammonia in methanol
  5. concentrationThe appropriate fraction is concentrated in vacuo

Sources & evidence

ORD record
ord-9d786f881e0d48e38a4c78c9281d797b
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Linked notes

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