Dimethylformamide → HCID 21890002, compound

HRID 721416Notes

Reaction equation

HRID 721416 reaction equation
[CH3:1]N(C)C=O.[H-].[Na+].[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:19]=1[O:20][CH3:21])[N:16]=[CH:15][N:14]=[C:13]2[O:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:38])[O:31][CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)=[CH:25][CH:24]=1.CI>O>[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:19]=1[O:20][CH3:21])[N:16]=[CH:15][N:14]=[C:13]2[O:22][C:23]1[CH:24]=[CH:25][C:26]([N:29]([CH3:1])[C:30](=[O:38])[O:31][CH:32]2[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]2)=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21890166HCID 21890166, compound

Product 1

HCID 21890002HCID 21890002, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dimethylformamide (5 ml) was added to sodium hydride (7 mg), and cyclohexyl N-{4-[(6,7-dimethoxy-4-quinazolinyl)oxy]phenyl}carbamate (35 mg) was added to the mixture. Subsequently, a dimethylformamide solution (2 ml) of methyl iodide (47 mg) was added thereto, and the mixture was stirred at room temperature for 10 min. Water was added to stop the reaction, and the reaction solution was then extracted with ethyl acetate, followed by washing with water and saturated brine in that order. The extract was dried over sodium sulfate and was then concentrated. The residue was purified on a column using chloroform/methanol to give the title compound (30 mg, yield 83%).

Workup

  1. additionwas added to the mixture
  2. customthe reaction
  3. extractionthe reaction solution was then extracted with ethyl acetate
  4. washby washing with water and saturated brine in that order
  5. dry with materialThe extract was dried over sodium sulfate
  6. concentrationwas then concentrated
  7. customThe residue was purified on a column

Sources & evidence

ORD record
ord-3fb116b6bde34bb9bd21a526e453d92a
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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