Dimethylformamide → HCID 21891182, compound

HRID 721421Notes

Reaction equation

HRID 721421 reaction equation
[CH3:1]N(C)C=O.[H-].[Na+].[Cl:8][C:9]1[CH:14]=[C:13]([O:15][C:16]2[C:25]3[C:20](=[CH:21][C:22]([O:28][CH3:29])=[C:23]([O:26][CH3:27])[CH:24]=3)[N:19]=[CH:18][N:17]=2)[CH:12]=[CH:11][C:10]=1[NH:30][C:31](=[O:40])[O:32][CH:33]([CH2:37][CH2:38][CH3:39])[CH2:34][CH2:35][CH3:36].CI>O>[Cl:8][C:9]1[CH:14]=[C:13]([O:15][C:16]2[C:25]3[C:20](=[CH:21][C:22]([O:28][CH3:29])=[C:23]([O:26][CH3:27])[CH:24]=3)[N:19]=[CH:18][N:17]=2)[CH:12]=[CH:11][C:10]=1[N:30]([CH3:1])[C:31](=[O:40])[O:32][CH:33]([CH2:37][CH2:38][CH3:39])[CH2:34][CH2:35][CH3:36]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21891215HCID 21891215, compound

Product 1

HCID 21891182HCID 21891182, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dimethylformamide (5 ml) was added to sodium hydride (11 mg), and 1-propylbutyl N-{2-chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]phenyl}carbamate (62 mg) was added to the mixture. Subsequently, a dimethylformamide solution (2 ml) of methyl iodide (77 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 (43 mg, yield 68%).

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-74a6c3723c8c4195896f84596781516e
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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