Sodium Chloride → HCID 22707480, compound

HRID 353154Notes

Reaction equation

HRID 353154 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.[CH3:38][S:39](Cl)(=[O:41])=[O:40].[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[C:9](=[CH:10][C:11]([NH:12][CH2:13][CH3:14])=[C:2]([NH:1][S:39]([CH3:38])(=[O:41])=[O:40])[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

7

Reactant 4

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2×HCID 11223943HCID 11223943, compound

Product 1

HCID 22707480HCID 22707480, compoundYield 6%

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 (1.55 mmol) of methanesulfonyl chloride, followed by overnight stirring at room temperature in an atmosphere of argon. To the resulting mixture was added 0.06 ml (0.31 mmol) of methanesulfonyl chloride, followed by overnight stirring at room temperature. 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 at room temperature
  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-74957dcdda4245c3b124d82b17433d12
Source dataset
uspto-grants-2004_06
Patent number
US06750218B2

Reaction notes

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