Pyridine → HCID 11305002, compound

HRID 353157Notes

Reaction equation

HRID 353157 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[NH:12][CH2:13][CH3:14])[N:8]=[CH:7][N:6]=[C:5]2[N:15]1[CH2:20][CH2:19][N:18]([C:21](=[S:30])[NH:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:17][CH2:16]1.N1C=CC=C[CH:32]=1.C(Cl)(=O)C(Cl)=O.[Cl-].[Na+]>CN(C)C=O.O>[CH2:23]([NH:22][C:21]([N:18]1[CH2:19][CH2:20][N:15]([C:5]2[C:4]3[CH:3]=[C:2]4[N:1]=[CH:32][N:12]([CH2:13][CH3:14])[C:11]4=[CH:10][C:9]=3[N:8]=[CH:7][N:6]=2)[CH2:16][CH2:17]1)=[S:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 5234Sodium ChlorideHCID 65578Oxalyl chlorideHCID 11223943HCID 11223943, compound

Product 1

HCID 11305002HCID 11305002, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 504.4 mg (1.20 mmol) of 4-(6-amino-7-ethylamino-4-quinazolinyl)-N-benzyl-1-piperazinethiocarboxamide obtained in Example 461 in 10 ml of dimethylformamide were added 0.29 ml (3.60 mmol) of pyridine and 0.13 ml (1.49 mmol) of oxalyl chloride under ice-cooling, followed by overnight stirring at room temperature in an atmosphere of argon. Then, the resulting mixture was heated at 80° C. with stirring for 5 hours. The reaction mixture was allowed to cool to room temperature and then 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. temperaturecooling
  2. temperatureThen, the resulting mixture was heated at 80° C.
  3. stirringwith stirring for 5 hours
  4. temperatureto cool to room temperature
  5. additionwas added
  6. filtrationThe precipitated crystals were collected by filtration
  7. washwashed with water
  8. customdried
  9. customfollowed by purification by silica gel chromatography

Sources & evidence

ORD record
ord-9519041027fa43a5a86d75f4be486448
Source dataset
uspto-grants-2004_06
Patent number
US06750218B2

Reaction notes

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