Sodium Chloride → HCID 11049200, compound

HRID 1533130Notes

Reaction equation

HRID 1533130 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[C:26]4[C:21](=[CH:22][C:23]([O:29][CH3:30])=[C:24]([O:27][CH3:28])[CH:25]=4)[N:20]=[CH:19][N:18]=3)[CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:33]I.[Cl-].[Na+]>CN(C)C=O.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:33])[C:9]([N:11]2[CH2:12][CH2:13][N:14]([C:17]3[C:26]4[C:21](=[CH:22][C:23]([O:29][CH3:30])=[C:24]([O:27][CH3:28])[CH:25]=4)[N:20]=[CH:19][N:18]=3)[CH2:15][CH2:16]2)=[O:10])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10457505HCID 10457505, compound

Product 1

HCID 11049200HCID 11049200, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.01 g (2.15 mmol) of N-(4-bromophenyl)-4-(6,7-dimethoxy-4-quinazolinyl)-1-piperazinecarboxamide obtained in Example 45 in 15 ml of dimethylformamide was added 171.9 mg (4.30 mmol) of 60% sodium hydride under ice-cooling, followed by stirring at room temperature for 30 minutes. To the reaction mixture was added 0.27 ml (4.34 mmol) of methyl iodide, followed by overnight stirring at room temperature. The resulting mixture was poured into water, and sodium chloride was added thereto. The precipitated crystals were collected by filtration, washed with water, and dried, followed by purification by silica gel column chromatography to give the desired compound as colorless crystals.

Workup

  1. temperaturecooling
  2. waitfollowed by overnight
  3. stirringstirring at room temperature
  4. additionwas added
  5. filtrationThe precipitated crystals were collected by filtration
  6. washwashed with water
  7. customdried
  8. customfollowed by purification by silica gel column chromatography

Sources & evidence

ORD record
ord-1f741c1a2fcf4be2ac877f2ce4f67180
Source dataset
uspto-grants-2001_03
Patent number
US06207667B1

Reaction notes

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