Water → HCID 86585282, compound

HRID 993178Notes

Reaction equation

HRID 993178 reaction equation
[NH2:1][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.[CH2:31]([N:33]=[C:34]=[S:35])[CH3:32].O.[Cl-].[Na+]>CN(C)C=O>[CH3:28][O:27][C:24]1[CH:25]=[C:26]2[C:21](=[CH:22][C:23]=1[O:29][CH3:30])[N:20]=[CH:19][N:18]=[C:17]2[N:14]1[CH2:13][CH2:12][N:11]([C:9]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:34]([NH:33][CH2:31][CH3:32])=[S:35])=[CH:3][CH:4]=2)=[O:10])[CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 10966Ethyl isothiocyanate2×HCID 22707383HCID 22707383, compound

Product 1

HCID 86585282HCID 86585282, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 514.0 mg (1.26 mmol) of N-(4-aminophenyl)-4-(6,7-dimethoxy-4-quinazolinyl)-1-piperazinecarboxamide obtained in Example 221 in 10 ml of dimethylformamide was added 0.13 ml (1.51 mmol) of ethyl isothiocyanate, followed by overnight stirring at room temperature. To the resulting mixture was added 0.13 ml (1.51 mmol) of ethyl isothiocyanate, followed by overnight stirring. The reaction 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 chromatography to give the desired compound as colorless crystals.

Workup

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

Sources & evidence

ORD record
ord-65e05a17b5e946debb11784f49d8ad87
Source dataset
uspto-grants-2002_10
Patent number
US06472391B2

Reaction notes

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