HCID 21864830, compound → 5-Chloro-N-[4-methoxy-3-(1-piperazinyl)phenyl]-3-methylbenzo[b]thiophene-2-sulfonamide hydrochloride

HRID 2230124Notes

Reaction equation

HRID 2230124 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]2[S:6][C:7]([S:10]([OH:13])(=[O:12])=O)=[C:8]([CH3:9])[C:4]=2[CH:3]=1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([NH-:24])=[CH:20][C:19]=1[N:25]1[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26]1>O1CCCC1.Cl>[ClH:1].[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][S:10]([C:7]2[S:6][C:5]3[CH:14]=[CH:15][C:2]([Cl:1])=[CH:3][C:4]=3[C:8]=2[CH3:9])(=[O:12])=[O:13])=[CH:20][C:19]=1[N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1

Participants

5

Reactant 2

HCID 21864830HCID 21864830, compoundHCID 86758376HCID 86758376, compound

Product 1

HCID 69184555-Chloro-N-[4-methoxy-3-(1-piperazinyl)phenyl]-3-methylbenzo[b]thiophene-2-sulfonamide hydrochloride

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred suspension of 5-chloro-3-methylbenzo[b]thiophene-2-sulfonic acid (4-methoxy-3-(4-tert-butoxycarbonylpiperazin-1-yl)phenylamide (D10) (193 g) in tetrahydrofuran (820 ml) and concentrated hydrochloric acid (180 ml) was heated at reflux for 1.75 h after which time a solution was obtained. The solution was concentrated and the residue dissolved in hot ethanol (600 ml). Upon cooling, a solid precipitated which was filtered and recrystallised (ethanol/water 1:1) to give the title compound (E83) as a white solid, m.p. 276-280° C. (dec.) (142 g, 83%). δH (250 MHz, D6-dmso) 2.29 (3H, s), 2.90 (4H, br s), 3.01 (4H, br s), 3.55 (3H, s), 6.54-6.71 (3H. m), 7.42 (1H, d, J 8.8 Hz), 7.85 (1H, s), 7.93 (1H, d, J 8.8 Hz), 9.03 (2H, br s), 10.3 (1H, br s). MH+ 452.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1.75 h after which time a solution
  3. customwas obtained
  4. concentrationThe solution was concentrated
  5. dissolutionthe residue dissolved in hot ethanol (600 ml)
  6. temperatureUpon cooling
  7. customa solid precipitated which
  8. filtrationwas filtered
  9. customrecrystallised (ethanol/water 1:1)

Sources & evidence

ORD record
ord-983c0d711a32405fb7f49d2fb52d9a8f
Source dataset
uspto-grants-2002_07
Patent number
US06423717B1

Reaction notes

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