Acetic Acid → HCID 23728822, compound

HRID 1619234Notes

Reaction equation

HRID 1619234 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.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.[BH3-]C#N.[Na+]>C1COCC1>[CH:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[S:11][C:12]3[CH:18]=[C:17]([CH2:19][N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)[CH:16]=[CH:15][C:13]=3[N:14]=2)[CH2:8][CH2:9]1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 5003444Sodium cyanoborohydrideHCID 59588785HCID 59588785, compound

Product 1

HCID 23728822HCID 23728822, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
63 °C

Procedure

To a solution of 2-(4-isopropylpiperazin-1-yl)benzothiazole-6-carboxaldehyde (0.5 g, 1.73 mmol) and AcOH (11 mg, 0.173 mmol) in THF (5 mL), morpholine (0.31 mL, 3.46 mmol) and NaCNBH3 (132 mg, 2.08 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 130 mg (21%) of 2-(4-isopropylpiperazin-1-yl)-6-(morpholin-4-ylmethyl)benzothiazole 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-c7eef08a63294194acb0ffe668ac5bec
Source dataset
uspto-grants-2014_07
Patent number
US08772285B2

Reaction notes

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