Benzenesulfonyl chloride → HCID 21905989, compound

HRID 1244285Notes

Reaction equation

HRID 1244285 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-aaaf9640d2144affaa99df26fcb62acb
Source dataset
uspto-grants-2006_10
Patent number
US07122544B2

Reaction notes

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