Acetic Acid → [2-(4-Isopropylpiperazin-1-yl)benzothiazol-5-yl-methyl]dimethylamine

HRID 1944690Notes

Reaction equation

HRID 1944690 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][C:16]([CH:19]=O)=[CH:15][C:13]=3[N:14]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].Cl.[CH3:22][NH:23][CH3:24].C(O)(=O)C.[BH3-]C#N.[Na+]>C1COCC1.CO>[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[S:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][N:23]([CH3:24])[CH3:22])=[CH:15][C:13]=3[N:14]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 10473Dimethylamine, hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 595887932-(4-Isopropylpiperazin-1-yl)benzothiazole-5-carbaldehyde

Product 1

HCID 23728895[2-(4-Isopropylpiperazin-1-yl)benzothiazol-5-yl-methyl]dimethylamineYield 46%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-isopropylpiperazin-1-yl)benzothiazole-5-carbaldehyde (500 mg, 1.73 mmol) and dimethylamine hydrochloride (282 mg, 3.46 mmol) in THF (27.5 mL) and MeOH (13.7 mL) was added acetic acid (166 mg, 2.77 mmol), followed by NaCNBH3 (160 mg, 2.77 mmol). The mixture was heated at reflux overnight. The mixture was concentrated under reduced pressure, neutralized with an aqueous solution of Na2CO3 to pH 7, and filtered. The residue was extracted with dichloromethane (3×10 mL). The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated. The residue was purified by preparative HPLC to give 251 mg (46%) of [2-(4-isopropylpiperazin-1-yl)benzothiazol-5-yl-methyl]dimethylamine as a trifluoroacetate salt.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. concentrationThe mixture was concentrated under reduced pressure
  4. filtrationfiltered
  5. extractionThe residue was extracted with dichloromethane (3×10 mL)
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-14e310191fc54dc695b3f6f65b401a9c
Source dataset
uspto-grants-2013_03
Patent number
US08394842B2

Reaction notes

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