Dimethylformamide → HCID 21890128, compound

HRID 721415Notes

Reaction equation

HRID 721415 reaction equation
CN(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:39])[O:32][CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1.[CH2:40](I)[CH3:41]>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]([CH2:40][CH3:41])[C:31](=[O:39])[O:32][CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 21890738HCID 21890738, compound

Product 1

HCID 21890128HCID 21890128, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dimethylformamide (5 ml) was added to sodium hydride (11 mg), and cyclohexyl N-{2-chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]phenyl}carbamate (65 mg) was added to the mixture. Subsequently, a dimethylformamide solution (2 ml) of ethyl iodide (87 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 (60 mg, yield 88%).

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-29aea1d5157f4d4a92f823768619029d
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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