Pyridine → HCID 59532407, compound

HRID 2424635Notes

Reaction equation

HRID 2424635 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@@H:11]([CH3:22])[CH2:10]2)=[C:4]([CH3:23])[CH:3]=1.N1C=CC=CC=1.[Cl:30][C:31]1[N:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=1>C(Cl)Cl.O.C(Cl)Cl>[Cl:30][C:31]1[N:36]=[CH:35][C:34]([S:37]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([CH2:8][N:9]3[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[C@@H:11]([CH3:22])[CH2:10]3)=[C:4]([CH3:23])[CH:3]=2)(=[O:39])=[O:38])=[CH:33][CH:32]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 27927922-Chloro-5-pyridinesulfonyl chlorideHCID 59262126tert-butyl (2S)-4-[(4-amino-2-methylphenyl)methyl]-2-methylpiperazine-1-carboxylate

Product 1

HCID 59532407HCID 59532407, compoundYield 106.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 21908982Water methylene chlorideSolvent

Procedure

D7 (100 mg, 0.31 mmol) in dry DCM (1.05 mL) and pyridine (0.30 mL, 3.8 mmol) was stirred to 0° C. under argon and 6-chloro-3-pyridinesulfonyl chloride (60 mg, 0.28 mmol) in dry DCM (1.05 mL) added dropwise. The reaction mixture was stirred under argon and allowed to warm to room temperature. After 17 h, the reaction mixture was diluted with water/DCM. The aqueous layer was extracted with DCM, the organic layer dried (Na2SO4) and solvent removed under vacuum. The product was purified by column chromatography (Biotage Horizon 40+S) eluting with petroleum ether/Et2O to afford the title compound as a colourless oil (148 mg). MS (ES+): MH+ 495.1/497.1.

Workup

  1. extractionThe aqueous layer was extracted with DCM
  2. dry with materialthe organic layer dried (Na2SO4) and solvent
  3. customremoved under vacuum
  4. customThe product was purified by column chromatography (Biotage Horizon 40+S)
  5. washeluting with petroleum ether/Et2O

Sources & evidence

ORD record
ord-8ef75575d93c4cf39b05c8bcc1a5c2b8
Source dataset
uspto-grants-2011_06
Patent number
US07964597B2

Reaction notes

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