Benzenesulfonyl chloride → HCID 21905989, compound

HRID 2117307Notes

Reaction equation

HRID 2117307 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19]3[N:24]=[C:23]([C:25]4[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=4)[CH:22]=[CH:21][N:20]=3)=[CH:14][CH:13]=2)=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[C:32]1([S:38](Cl)(=[O:40])=[O:39])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]([C:12]2[CH:13]=[CH:14][C:15]([NH:18][C:19]3[N:24]=[C:23]([C:25]4[CH:26]=[CH:27][C:28]([NH:31][S:38]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)(=[O:40])=[O:39])=[CH:29][CH:30]=4)[CH:22]=[CH:21][N:20]=3)=[CH:16][CH:17]=2)=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 219060081-Acetyl-4-[(4-{[4-(4-aminophenyl)pyrimidin-2-yl}amino}phenyl)carbonyl}piperazine

Product 1

HCID 21905989HCID 21905989, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution of 1-acetyl-4-[(4-{[4-(4-aminophenyl)pyrimidin-2-yl}amino}phenyl)carbonyl}piperazine (100 mg, 0.24 mmol) in pyridine (5 mL) containing a catalytic amount of DMAP is added benzenesulfonyl chloride (50 mg, 0.29 mmol) and the solution is stirred overnight at room temperature. The pyridine is removed under vacuum and the residue extracted into methylene chloride and washed with 1N HCl. Evaporation of solvent provides the crude piperazine which is purified by preparative HPLC (10-60% CH3CN over 25 min.)to give an analytically pure sample as a yellow solid: M+1; 557.3. HPLC Retention Time; 9.59 min (Method B).

Workup

  1. customThe pyridine is removed under vacuum
  2. extractionthe residue extracted into methylene chloride
  3. washwashed with 1N HCl
  4. customEvaporation of solvent

Sources & evidence

ORD record
ord-7a675003da124fe18604c884fa22d74a
Source dataset
uspto-grants-2008_10
Patent number
US07442699B2

Reaction notes

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