Acetic Acid → HCID 23728823, compound

HRID 1619235Notes

Reaction equation

HRID 1619235 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[S:11][C:12]3[CH:18]=[C:17]([CH:19]=O)[CH:16]=[CH:15][C:13]=3[N:14]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].CC(O)=O.Cl.[CH3:26][NH:27][CH3:28].[BH3-]C#N.[Na+]>C1COCC1>[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[S:11][C:12]3[CH:18]=[C:17]([CH2:19][N:27]([CH3:28])[CH3:26])[CH:16]=[CH:15][C:13]=3[N:14]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 10473Dimethylamine, hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 59588785HCID 59588785, compound

Product 1

HCID 23728823HCID 23728823, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
63 °C

Procedure

To a solution of 2-(4-isopropylpiperazin-1-yl)benzothiazole-6-carboxaldehyde (0.7 g, 2.42 mmol) and AcOH (291 mg, 4.84 mmol) in THF, dimethylamine hydrochloride (397 mg, 4.84 mmol) and NaCNBH3 (245 mg, 3.88 mmol) were added in turn. The reaction mixture was heated at 63° C. for 12 hours. The solvent was removed and the residue was extracted with ethyl acetate, washed with water and brine and dried (MgSO4). The volatiles were evaporated and the residue was purified by preparative HPLC to yield 250 mg (32%) of [2-(4-isopropylpiperazin-1-yl)benzothiazol-6-ylmethyl]dimethylamine as a trifluoroacetate salt.

Workup

  1. customThe solvent was removed
  2. extractionthe residue was extracted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. customThe volatiles were evaporated
  6. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-29e0cc32db5e4b3dae23712739b8ed80
Source dataset
uspto-grants-2014_07
Patent number
US08772285B2

Reaction notes

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