5-Chloro-3-methylbenzo(b)thiophene-2-sulfonyl chloride → HCID 18180112, compound

HRID 1358960Notes

Reaction equation

HRID 1358960 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:16])[CH:6]=[CH:7][C:8]=1[N:9]1[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]1.[Cl:17][C:18]1[CH:31]=[CH:30][C:21]2[S:22][C:23]([S:26](Cl)(=[O:28])=[O:27])=[C:24]([CH3:25])[C:20]=2[CH:19]=1>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:16][S:26]([C:23]2[S:22][C:21]3[CH:30]=[CH:31][C:18]([Cl:17])=[CH:19][C:20]=3[C:24]=2[CH3:25])(=[O:28])=[O:27])[CH:6]=[CH:7][C:8]=1[N:9]1[CH2:10][CH2:11][N:12]([CH3:15])[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 27357565-Chloro-3-methylbenzo(b)thiophene-2-sulfonyl chlorideHCID 118447613-Methoxy-4-(4-methylpiperazin-1-yl)aniline

Product 1

HCID 18180112HCID 18180112, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-methoxy-4-(4-methylpiperazin-1-yl)phenylamine (D35) (50 mg, 0.23 mmol) and 5-chloro-3-methylbenzo[b]thiophene-2-sulfonyl chloride (64 mg, 0.23 mmol) in dichloromethane (2 ml) was allowed to stand at room temperature overnight. The reaction mixture was diluted with dichloromethane and washed with potassium carbonate (aq), which was back-extracted with further dichloromethane. The combined organic phases were dried (Na2SO4) and evaporated under reduced pressure to give a crude product, which was purified by chromatography on silica gel, eluting with methanol and dichloromethane. This gave the title compound (E128) as an off-white solid (36 mg, 34%) MH+=466.

Workup

  1. washwashed with potassium carbonate (aq), which
  2. extractionwas back-extracted with further dichloromethane
  3. dry with materialThe combined organic phases were dried (Na2SO4)
  4. customevaporated under reduced pressure
  5. customto give a crude product, which
  6. customwas purified by chromatography on silica gel
  7. washeluting with methanol and dichloromethane

Sources & evidence

ORD record
ord-e63ee4a5cb2449c883e15be37e900b42
Source dataset
uspto-grants-2003_07
Patent number
US06599904B2

Reaction notes

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