Acetic Acid → HCID 23728856, compound

HRID 1619246Notes

Reaction equation

HRID 1619246 reaction equation
[CH:1]1([N:4]2[CH2:9][CH2:8][N:7]([C:10]3[S:11][C:12]4[CH:18]=[C:17]([CH:19]=O)[CH:16]=[CH:15][C:13]=4[N:14]=3)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1.[NH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.C(O)(=O)C.[BH3-]C#N.[Na+]>CO.C1COCC1>[CH:1]1([N:4]2[CH2:9][CH2:8][N:7]([C:10]3[S:11][C:12]4[CH:18]=[C:17]([CH2:19][N:21]5[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]5)[CH:16]=[CH:15][C:13]=4[N:14]=3)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 5003444Sodium cyanoborohydrideHCID 59588794HCID 59588794, compound

Product 1

HCID 23728856HCID 23728856, compoundYield 54.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
63 °C

Procedure

To a solution of 2-(4-cyclopropylpiperazin-1-yl)benzothiazole-6-carboxaldehyde (500 mg, 1.7 mmol) in MeOH (14 mL) and THF (28 mL) was added piperidine (290 mg, 3.4 mmol), acetic acid (22 mg, 0.4 mmol) and NaCNBH3 (158 mg, 2.7 mmol). The mixture was stirred at 63° C. overnight. The reaction mixture was concentrated under reduced pressure and CH2Cl2 (15 mL) was added to the residue. The mixture was washed with brine, dried (MgSO4) and concentrated under reduced pressure. The residue was purified by preparative HPLC to give 332 mg (28%) of 2-(4-cyclopropylpiperazin-1-yl)-6-(piperidin-1-ylmethyl)benzothiazole as a trifluoroacetate salt.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure and CH2Cl2 (15 mL)
  2. additionwas added to the residue
  3. washThe mixture was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-21ca9527213441adaeee0fc66d3ab9ec
Source dataset
uspto-grants-2014_07
Patent number
US08772285B2

Reaction notes

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