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Hydrochloric Acid → 4-(2-Diisopropylamino-ethylamino)benzenesulfonic acid 2-butyrylaminobenzothiazol-6-yl ester hydrochloride

HRID 1867993
Notes
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Reaction equation

HRID 1867993 reaction equation
[C:1]([NH:6][C:7]1[S:8][C:9]2[CH:15]=[C:14]([O:16][S:17]([C:20]3[CH:25]=[CH:24][C:23](F)=[CH:22][CH:21]=3)(=[O:19])=[O:18])[CH:13]=[CH:12][C:10]=2[N:11]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].[CH:27]([N:30]([CH:34]([CH3:36])[CH3:35])[CH2:31][CH2:32][NH2:33])([CH3:29])[CH3:28].[ClH:37]>CN1CCCC1=O.C(OCC)(=O)C.O1CCOCC1>[ClH:37].[C:1]([NH:6][C:7]1[S:8][C:9]2[CH:15]=[C:14]([O:16][S:17]([C:20]3[CH:25]=[CH:24][C:23]([NH:33][CH2:32][CH2:31][N:30]([CH:34]([CH3:36])[CH3:35])[CH:27]([CH3:29])[CH3:28])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[CH:13]=[CH:12][C:10]=2[N:11]=1)(=[O:5])[CH2:2][CH2:3][CH3:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 84591,2-Ethanediamine, N1,N1-bis(1-methylethyl)-HCID 579807964-Fluorobenzenesulfonic acid 2-butyrylaminobenzothiazol-6-yl ester2×

Product 1

HCID 866121524-(2-Diisopropylamino-ethylamino)benzenesulfonic acid 2-butyrylaminobenzothiazol-6-yl ester hydrochlorideYield 28%

Reagents, catalysts & solvents 3

HCID 8857
Ethyl Acetate
Solvent
HCID 13387N-methyl-2-pyrrolidoneSolvent
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

A solution of 4-fluorobenzenesulfonic acid 2-butyrylaminobenzothiazol-6-yl ester (intermediate 78) (100 mg, 0.2 mmol) and N,N-diisopropylethylene-diamine (185 μl, 1.01 mmol) in 3 ml of N-methylpyrrolidone in a 5 ml microwave vial, equipped with a magnetic bar, is heated for 10 minutes at 150° C. by microwave. The reaction medium is extracted with ethyl acetate and washed with water. The organic phase is dried over magnesium sulfate, filtered and then evaporated to dryness. The residue obtained is purified by chromatography on Merck silica (40-63 μm). After evaporating off the solvent, 41 mg of a colorless oil (crystallizes when dry) are obtained. The product is dissolved in a minimum amount of ethyl acetate, and 4 N hydrochloric acid as a solution in dioxane is then added. The medium precipitates, and is concentrated, taken up in water and then filtered through a Milex 45 μm filter. The solution precipitates, and 31 mg (28% yield) of 4-(2-diisopropylamino-ethylamino)benzenesulfonic acid 2-butyrylaminobenzothiazol-6-yl ester hydrochloride are obtained after vacuum filtration and then drying under vacuum at 40° C.

Workup

  1. extractionThe reaction medium is extracted with ethyl acetate
  2. washwashed with water
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue obtained
  7. customis purified by chromatography on Merck silica (40-63 μm)
  8. customAfter evaporating off the solvent, 41 mg of a colorless oil (crystallizes when dry)
  9. customare obtained
  10. additionis then added
  11. customThe medium precipitates
  12. concentrationis concentrated
  13. filtrationfiltered through a Milex 45 μm
  14. filtrationfilter
  15. customThe solution precipitates

Sources & evidence

ORD record
ord-d1deb372ac8547c0951405d7c3ecc000
Source dataset
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07632952B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes