2-Chloro-5-pyridinesulfonyl chloride → 1,1-Dimethylethyl (2S)-4-({4-[[(6-chloro-3-pyridinyl)sulfonyl](methyl)amino]-2-methylphenyl}methyl)-2-methyl-1-piperazinecarboxylate

HRID 2424636Notes

Reaction equation

HRID 2424636 reaction equation
[CH3:1][C@H:2]1[CH2:7][N:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][CH3:16])=[CH:11][C:10]=2[CH3:17])[CH2:5][CH2:4][N:3]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][N:27]=1>>[Cl:25][C:26]1[N:27]=[CH:28][C:29]([S:32]([N:15]([CH3:16])[C:12]2[CH:13]=[CH:14][C:9]([CH2:8][N:6]3[CH2:5][CH2:4][N:3]([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[C@@H:2]([CH3:1])[CH2:7]3)=[C:10]([CH3:17])[CH:11]=2)(=[O:34])=[O:33])=[CH:30][CH:31]=1

Participants

3

Reactant 2

HCID 27927922-Chloro-5-pyridinesulfonyl chlorideHCID 59262129tert-butyl (2S)-2-methyl-4-[2-methyl-4-(methylamino)benzyl]piperazine-1-carboxylate

Product 1

HCID 595323961,1-Dimethylethyl (2S)-4-({4-[[(6-chloro-3-pyridinyl)sulfonyl](methyl)amino]-2-methylphenyl}methyl)-2-methyl-1-piperazinecarboxylate

Procedure

The title compound was prepared from D8 and 2-chloropyridine-5-sulfonyl chloride using a method similar to that described for D15 except that the reaction time was overnight. The work-up involved concentration of the reaction mixture and purification by elution through an SCX cartridge (MeOH then 0.2M NH3 in MeOH), followed by column chromatography eluting with 0-20% EtOAc/petroleum ether. δH (CDCl3, 400 MHz) 8.55 (1H, dd), 7.76 (1H, dd), 7.42 (1H, d), 7.21 (1H, d), 6.96 (1H, d), 6.80 (1H, dd), 6.86 (1H, dd), 4.20 (1H, br.s), 3.79 (1H, m), 3.38 (2H, AB), 3.20 (3H, s), 3.05 (1H, m), 2.69 (1H, m), 2.56 (1H, m), 2.32 (3H, s), 2.19 (1H, m), 1.99 (1H, m), 1.46 (9H, s), 1.21 (3H, d). MS (ES+): MH+ 509/511.

Workup

  1. concentrationThe work-up involved concentration of the reaction mixture and purification
  2. washby elution through an SCX cartridge (MeOH
  3. washeluting with 0-20% EtOAc/petroleum ether

Sources & evidence

ORD record
ord-03ec925414bc4a02bd3c04d80d582e9c
Source dataset
uspto-grants-2011_06
Patent number
US07964597B2

Reaction notes

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