Methyl iodide → HCID 69667378, compound

HRID 1241897Notes

Reaction equation

HRID 1241897 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[C:16]2[CH2:15][CH2:14][N:13]([C:17]3[CH:22]=[CH:21][C:20]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:19][CH:18]=3)[C:12](=[O:31])[C:11]=2[N:10]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[CH:33]=2)[N:9]=1)=[O:7])[CH3:4].[CH3:39]I>CN(C=O)C>[CH2:3]([O:5][C:6]([C:8]1[C:16]2[CH2:15][CH2:14][N:13]([C:17]3[CH:18]=[CH:19][C:20]([N:23]([C:24]([O:26][C:27]([CH3:30])([CH3:28])[CH3:29])=[O:25])[CH3:39])=[CH:21][CH:22]=3)[C:12](=[O:31])[C:11]=2[N:10]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[CH:33]=2)[N:9]=1)=[O:7])[CH3:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 69667199HCID 69667199, compound

Product 1

HCID 69667378HCID 69667378, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

Part D. In a 200 mL of flask was placed 60% sodium hydride (0.23 g, 5.69 mmol) and DMF (10 mL). After being cooled to 0° C., a solution of 6-(4-tert-butoxycarbonylamino-phenyl)-1-(3-chloro-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester (1.45 g, 2.84 mmol) in DMF (5 mL) was then added. The reaction was stirred for 30 min and then treated with methyl iodide (0.86 g, 5.69 mmol). The reaction was allowed to stir at rt overnight. After quenching with water, the mixture was extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried with sodium sulfate, and concentrated to give 6-[4-(tert-butoxycarbonyl-methyl-amino)-phenyl]-1-(3-chloro-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester (1.12 g). APCI MS m/z 525 (M++1).

Workup

  1. customIn a 200 mL of flask was placed
  2. stirringto stir at rt overnight
  3. customAfter quenching with water
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6165582f48064b64a28aade850e44d5e
Source dataset
uspto-grants-2006_10
Patent number
US07115627B2

Reaction notes

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