Diethylcarbamoyl chloride → HCID 136403439, compound

HRID 1685134Notes

Reaction equation

HRID 1685134 reaction equation
O[C:2]1[C:3]([C:23]2[CH:28]=[CH:27][C:26]([C:29]3[CH:30]=[N:31][C:32]([C:35](=[O:38])[NH:36][CH3:37])=[CH:33][CH:34]=3)=[CH:25][CH:24]=2)=[N:4][N:5]([CH3:22])[C:6]=1[C:7]1[NH:21][C:10]2=[CH:11][C:12]3[CH2:13][N:14](C([O-])=O)[CH2:15][C:16]=3[CH:17]=[C:9]2[N:8]=1.CC(C)([O-:42])C.[K+].[CH2:45]([N:47]([CH2:51][CH3:52])[C:48](Cl)=[O:49])[CH3:46]>CN(C)C=O.C(OCC)(=O)C>[CH2:45]([N:47]([CH2:51][CH3:52])[C:48](=[O:42])[O:49][C:2]1[C:3]([C:23]2[CH:24]=[CH:25][C:26]([C:29]3[CH:30]=[N:31][C:32]([C:35](=[O:38])[NH:36][CH3:37])=[CH:33][CH:34]=3)=[CH:27][CH:28]=2)=[N:4][N:5]([CH3:22])[C:6]=1[C:7]1[NH:8][C:9]2=[CH:17][C:16]3[CH2:15][NH:14][CH2:13][C:12]=3[CH:11]=[C:10]2[N:21]=1)[CH3:46]

Participants

6

Reactant 3

HCID 6916Diethylcarbamoyl chlorideHCID 23665647Potassium tert-butoxideHCID 136403440HCID 136403440, compound

Product 1

HCID 136403439HCID 136403439, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(4-hydroxy-1-methyl-3-(4-(6-(methylcarbamoyl)pyridin-3-yl)phenyl)-1H-pyrazol-5-yl)-5,7-dihydroimidazo[4,5-f]isoindole-6(1H)-carboxylate 1-16 (63 mg, 0.11 mmol) in anhydrous N,N-dimethylformamide (2 mL) was added potassium tert-butoxide (25 mg, 0.22 mmol) and diethylcarbamoyl chloride (21 mg, 0.15 mmol). The reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was diluted with ethyl acetate. The organic layer was washed with water and saturated brine. The organic layer was dried over sodium sulfate. Solvent was evaporated under reduced pressure. To the residue was added a 30% solution of trifluoroacetic acid in dichloromethane (4 mL). The reaction mixture was stirred at room temperature for 2 hours. Solvent was evaporated under reduced pressure. The crude product was purified by RP-HPLC to afford the desired 1-methyl-3-(4-(6-(methylcarbamoyl)pyridin-3-yl)phenyl)-5-(1,5,6,7-tetrahydroimidazo[4,5-f]isoindol-2-yl)-1H-pyrazol-4-yl diethylcarbamate T-17 (48 mg, 0.085 mmol).

Workup

  1. washThe organic layer was washed with water and saturated brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customSolvent was evaporated under reduced pressure
  4. additionTo the residue was added a 30% solution of trifluoroacetic acid in dichloromethane (4 mL)
  5. stirringThe reaction mixture was stirred at room temperature for 2 hours
  6. customSolvent was evaporated under reduced pressure
  7. customThe crude product was purified by RP-HPLC

Sources & evidence

ORD record
ord-edc4310580624c3498b2ee81124e30b9
Source dataset
uspto-grants-2012_04
Patent number
US08148363B2

Reaction notes

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