Sodium Chloride → HCID 22707704, compound

HRID 353151Notes

Reaction equation

HRID 353151 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.C(N(CC)CC)C.[C:38](OC(=O)C)(=[O:40])[CH3:39].[Cl-].[Na+]>CN(C)C=O.O>[C:38]([NH: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)(=[O:40])[CH3:39]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 11223943HCID 11223943, compound

Product 1

HCID 22707704HCID 22707704, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 528 mg (1.25 mmol) of 4-(6-amino-7-ethylamino-4-quinazolinyl)-N-benzyl-1-piperazinethiocarboxamide obtained in Example 461 in 15 ml of dimethylformamide were added 0.57 ml (4.09 mmol) of triethylamine and 0.31 ml (3.29 mmol) of acetic anhydride, followed by overnight stirring at room temperature in an atmosphere of argon. 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. additionwas added
  2. filtrationThe precipitated crystals were collected by filtration
  3. washwashed with water
  4. customdried
  5. customfollowed by purification by silica gel chromatography

Sources & evidence

ORD record
ord-ed6dd402bc194fb5a5817f3a2636071c
Source dataset
uspto-grants-2004_06
Patent number
US06750218B2

Reaction notes

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