Water → HCID 22707380, compound

HRID 993183Notes

Reaction equation

HRID 993183 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.[CH2:31]([N:33]=[C:34]=S)[CH3:32].[OH2:36].[Cl-].[Na+]>CN(C)C=O>[CH2:23]([NH:22][C:21]([N:18]1[CH2:19][CH2:20][N:15]([C:5]2[C:4]3[C:9](=[CH:10][C:11]([NH:12][CH2:13][CH3:14])=[C:2]([NH:1][C:34]([NH:33][CH2:31][CH3:32])=[O:36])[CH:3]=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

6

Reactant 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 10966Ethyl isothiocyanate2×HCID 11223943HCID 11223943, compound

Product 1

HCID 22707380HCID 22707380, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 502.5 mg (1.19 mmol) of 4-(6-amino-7-ethylamino-4-quinazolinyl)-N-benzyl-1-piperazinethiocarboxamide obtained in Example 461 in 10 ml of dimethylformamide was added 0.10 ml (1.19 mmol) of ethyl isothiocyanate, followed by overnight stirring at room temperature. To the resulting mixture was added 0.10 ml (1.19 mmol) of ethyl isothiocyanate, followed by heating at 80° C. with stirring for 4 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. temperatureby heating at 80° C.
  2. stirringwith stirring for 4 hours
  3. temperatureto cool to 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 chromatography

Sources & evidence

ORD record
ord-2510782be9b44fe8abbd7f33fb55cd3f
Source dataset
uspto-grants-2002_10
Patent number
US06472391B2

Reaction notes

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