Acetic Acid → Azetidin-1-yl(7-(piperazin-1-yl)benzofuran-2-yl)methanone

HRID 383834

Reaction equation

HRID 383834 reaction equation
[N:1]1([C:5]([C:7]2[O:8][C:9]3[C:15]([N:16]4[CH2:21][CH2:20][N:19](CC5C=CC=CC=5)[CH2:18][CH2:17]4)=[CH:14][CH:13]=[CH:12][C:10]=3[CH:11]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.C(O)(=O)C.N>>[N:1]1([C:5]([C:7]2[O:8][C:9]3[C:15]([N:16]4[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]4)=[CH:14][CH:13]=[CH:12][C:10]=3[CH:11]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 222AmmoniaHCID 59636710Azetidin-1-yl(7-(4-benzylpiperazin-1-yl)benzofuran-2-yl)methanone

Product 1

HCID 59636763Azetidin-1-yl(7-(piperazin-1-yl)benzofuran-2-yl)methanone

Procedure

The compound was prepared according to the procedure disclosed in Example 39d starting from azetidin-1-yl(7-(4-benzylpiperazin-1-yl)benzofuran-2-yl)methanone (0.52 g, 1.38 mmol) and acetic acid (0.63 mL, 11.1 mmol). A solution of ammonia (3 mL, 7N in MeOH) was added to the mixture after the reaction was complete. The solvent was removed by rotary evaporation. The crude product was purified by flash chromatography (SiO2; gradient 0-10% ammonia (7N in MeOH) in DCM). Yield: 0.36 g (91%).

Workup

  1. customThe compound was prepared
  2. customThe solvent was removed by rotary evaporation
  3. customThe crude product was purified by flash chromatography (SiO2; gradient 0-10% ammonia (7N in MeOH) in DCM)

Sources & evidence

ORD record
ord-97d8016b45934f8389c9ddd985f0c489
Source dataset
uspto-grants-2013_02
Patent number
US08367676B2

Linked notes

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