4-Bromo-2-chlorobenzenesulfonyl chloride → HCID 58988150, compound

HRID 2234978Notes

Reaction equation

HRID 2234978 reaction equation
[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[N:14]=[C:13]([NH2:15])[C:12]([O:16][CH3:17])=[CH:11][CH:10]=2)[CH2:3]1.[Br:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[C:21]([Cl:29])[CH:20]=1>N1C=CC=CC=1.ClCCl>[Br:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([NH:15][C:13]2[C:12]([O:16][CH3:17])=[CH:11][CH:10]=[C:9]([N:4]3[CH2:3][C@H:2]([CH3:1])[NH:7][C@H:6]([CH3:8])[CH2:5]3)[N:14]=2)(=[O:26])=[O:27])=[C:21]([Cl:29])[CH:20]=1

Participants

5

Reactant 2

HCID 27347664-Bromo-2-chlorobenzenesulfonyl chlorideHCID 58988130HCID 58988130, compound

Product 1

HCID 58988150HCID 58988150, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

6-[cis-3,5-dimethyl-1-piperazinyl]-3-(methyloxy)-2-pyridinamine (D7, Method C) (473 mg, 2 mmol) was dissolved in pyridine (5 ml) and dichloromethane (5 ml). 4-Bromo-2-chlorobenzene sulfonyl chloride (870 mg, 3 mmol) was added and the solution stirred at room temperature for 5 hours. The mixture was concentrated in vacuo and azeotroped with methanol. The residue was loaded on to an SCX cartridge (Varian, 10 g) in methanol, washed with methanol and the basic products eluted with 2M ammonia/methanol. The product containing fractions were concentrated in vacuo and purified by flash chromatography (Biotage SP4, 40+S, 0-20% 2M ammonia/methanol in dichloromethane to afford the title product (D11), 478 mg, MS (ES+) m/e 489/491/493 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customazeotroped with methanol
  3. washwashed with methanol
  4. washthe basic products eluted with 2M ammonia/methanol
  5. additionThe product containing fractions
  6. concentrationwere concentrated in vacuo
  7. custompurified by flash chromatography (Biotage SP4, 40+S, 0-20% 2M ammonia/methanol in dichloromethane

Sources & evidence

ORD record
ord-8a453bde0dd74957aab08a77fcb9ee7a
Source dataset
uspto-grants-2010_05
Patent number
US07713978B2

Reaction notes

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