Hydrochloric Acid → 4-(2-Hydroxy-2-methylpropylamino)benzenesulfonic acid 2-butyrylaminobenzothiazol-6-yl ester hydrochloride

HRID 1867994Notes

Reaction equation

HRID 1867994 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].[NH2:27][CH2:28][C:29]([CH3:32])([OH:31])[CH3:30].[ClH:33]>CN1CCCC1=O.O1CCOCC1>[ClH:33].[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:27][CH2:28][C:29]([OH:31])([CH3:32])[CH3:30])=[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]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 951022-Propanol, 1-amino-2-methyl-HCID 579807964-Fluorobenzenesulfonic acid 2-butyrylaminobenzothiazol-6-yl ester2×

Product 1

HCID 866121534-(2-Hydroxy-2-methylpropylamino)benzenesulfonic acid 2-butyrylaminobenzothiazol-6-yl ester hydrochlorideYield 25%

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
150 °C

Procedure

A solution of 4-fluorobenzenesulfonic acid 2-butyrylaminobenzothiazol-6-yl ester (intermediate 78) (135 mg, 0.34 mmol) and 1-amino-2-methylpropan-2-ol (153 mg, 1.718 mmol) in 3 ml of N-methylpyrrolidone in a 5 ml microwave vial, equipped with a magnetic bar, is heated for 20 minutes at 150° C. by microwave. The reaction medium is extracted with ethyl acetate (3×20 ml) and washed with water (4×25 ml). The organic phase is dried over magnesium sulfate, filtered and then evaporated to dryness. The residue obtained is purified by chromatography on silica, on an 8 g 15-35 μm AIT column, eluting with a 9/1 ethyl acetate/cyclohexane mixture. After evaporating off the solvent, 55 mg of a colorless solid are obtained. The product is dissolved in a minimum amount of dioxane, and 4 N hydrochloric acid dissolved in dioxane is added. The precipitate obtained is filtered off by suction, washed with dioxane and then dried under vacuum at 40° C. to give 42 mg of 4-(2-hydroxy-2-methylpropylamino)benzenesulfonic acid 2-butyrylaminobenzothiazol-6-yl ester hydrochloride, i.e. a yield of 25%.

Workup

  1. extractionThe reaction medium is extracted with ethyl acetate (3×20 ml)
  2. washwashed with water (4×25 ml)
  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 silica, on an 8 g 15-35 μm AIT column
  8. washeluting with a 9/1 ethyl acetate/cyclohexane mixture
  9. customAfter evaporating off the solvent, 55 mg of a colorless solid
  10. customare obtained
  11. additionis added
  12. customThe precipitate obtained
  13. filtrationis filtered off by suction
  14. washwashed with dioxane
  15. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-3a51f42b85ac4682ae9ecd8732845518
Source dataset
uspto-grants-2009_12
Patent number
US07632952B2

Reaction notes

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