Diisopropylethylamine → 1-[(5-Chloro-1-phenylsulfonylindol-2-yl)sulfonyl]-4-[5-(2-methylpyridin-4-yl)thiazol-2-yl]piperazine

HRID 352930Notes

Reaction equation

HRID 352930 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[C:7]([C:9]2[S:13][C:12]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)=[N:11][CH:10]=2)[CH:6]=[CH:5][N:4]=1.[Cl:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[N:26]([S:30]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=[O:32])=[O:31])[C:25]([S:39](Cl)(=[O:41])=[O:40])=[CH:24]2.C(N(C(C)C)CC)(C)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[N:26]([S:30]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=[O:31])=[O:32])[C:25]([S:39]([N:17]1[CH2:18][CH2:19][N:14]([C:12]3[S:13][C:9]([C:7]4[CH:6]=[CH:5][N:4]=[C:3]([CH3:2])[CH:8]=4)=[CH:10][N:11]=3)[CH2:15][CH2:16]1)(=[O:41])=[O:40])=[CH:24]2

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 227108271-[5-(2-Methylpyridin-4-yl)thiazol-2-yl]piperazine hydrochlorideHCID 235137375-Chloro-1-phenylsulfonylindole-2-sulfonyl chloride

Product 1

HCID 227094921-[(5-Chloro-1-phenylsulfonylindol-2-yl)sulfonyl]-4-[5-(2-methylpyridin-4-yl)thiazol-2-yl]piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A saturated solution of hydrochloride in methanol (12 ml) was added to 1-(t-butoxycarbonyl)-4-[5-(2-methylpyridin-4-yl)thiazol-2-yl]piperazine (400 mg) at room temperature. After stirring for 10 minutes, the reaction mixture was concentrated under reduced pressure, whereby 1-[5-(2-methylpyridin-4-yl)thiazol-2-yl]piperazine hydrochloride was obtained as a white solid. In a solution of the resulting hydrochloride in methylene chloride (12 ml) was dissolved 5-chloro-1-phenylsulfonylindol-2-sulfonyl chloride (522 mg), followed by the addition of diisopropylethylamine (538 μl) at room temperature. After stirring for 3 hours, a saturated aqueous solution (50 ml) of sodium bicarbonate was added to the reaction. mixture to separate it into layers. The water layer was extracted with methylene chloride (2×15 ml). The organic layers were combined, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (methylene chloride:acetone=7:1), whereby the title compound (240 mg) was obtained as a foam.

Workup

  1. custommixture to separate it into layers
  2. extractionThe water layer was extracted with methylene chloride (2×15 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customThe residue was purified by chromatography on a silica gel column (methylene chloride:acetone=7:1), whereby the title compound (240 mg)
  7. customwas obtained as a foam

Sources & evidence

ORD record
ord-7bdf16dc4f9244a1b70e7fbfc4ee8390
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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