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Dimethylformamide → 5-(1,1-Dioxo-1lambda6-iso-thiazolidin-2-ylmethyl)-2-(4-isopropylpiperazin-1-yl)benzothiazole

HRID 1944693
Notes
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Reaction equation

HRID 1944693 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[S:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[H-].[Na+].Cl[CH2:22][CH2:23][CH2:24][S:25]([OH:28])(=O)=[O:26].[CH3:29][N:30](C=O)C>>[O:26]=[S:25]1(=[O:28])[CH2:24][CH2:23][CH2:22][N:30]1[CH2:29][C:16]1[CH:17]=[CH:18][C:12]2[S:11][C:10]([N:7]3[CH2:6][CH2:5][N:4]([CH:1]([CH3:3])[CH3:2])[CH2:9][CH2:8]3)=[N:14][C:13]=2[CH:15]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 1709623-chloropropane-1-sulfonic AcidHCID 106114582-(4-Isopropylpiperazin-1-yl)benzothiazole

Product 1

HCID 237289355-(1,1-Dioxo-1lambda6-iso-thiazolidin-2-ylmethyl)-2-(4-isopropylpiperazin-1-yl)benzothiazoleYield 45%

Procedure

To a solution of 5-aminomethyl-[2-(4-isopropylpiperazin-1-yl)benzothiazole (439 mg, 1.51 mmol) in DMF (10 mL) was added NaH (181 mg, 4.53 mmol) at 0° C. The mixture was allowed to warm to rt. After 30 min, a solution of 3-chloropropane-1-sulfonic acid (373 mg, 2.11 mmol) in DMF (1.67 mL) was added at rt. The reaction mixture was stirred at rt for 2 h and then quenched with water. The volatiles were removed and the residue was extracted with ethyl acetate. The organic extract was washed with brine and concentrated. The residue was purified by the preparative HPLC to give 267 mg (45%) of 5-(1,1-dioxo-1λ6-isothiazolidin-2-ylmethyl)-2-(4-isopropylpiperazin-1-yl)benzothiazole as a trifluoroacetate salt.

Workup

  1. customquenched with water
  2. customThe volatiles were removed
  3. extractionthe residue was extracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with brine
  6. concentrationconcentrated
  7. customThe residue was purified by the preparative HPLC

Sources & evidence

ORD record
ord-026b79a52eef4e8082c9941a36e728ef
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08394842B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes