Dimethylformamide → 4-(6-Chloronaphthalene-2-sulphonyl)-1-[4-(2-methoxyethoxycarbonylamino)-1-(4-pyridyl)-4-piperidylmethyl]-2-piperazinone

HRID 2214822Notes

Reaction equation

HRID 2214822 reaction equation
[NH2:1][C:2]1([CH2:14][N:15]2[CH2:20][CH2:19][N:18]([S:21]([C:24]3[CH:33]=[CH:32][C:31]4[C:26](=[CH:27][CH:28]=[C:29]([Cl:34])[CH:30]=4)[CH:25]=3)(=[O:23])=[O:22])[CH2:17][C:16]2=[O:35])[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[C:36](=[O:52])([O-])[O:37][C:38]1[CH:43]=CC([N+]([O-])=O)=CC=1CCOC.C(N(C(C)C)C(C)C)C.CN([CH:65]=[O:66])C>>[Cl:34][C:29]1[CH:30]=[C:31]2[C:26](=[CH:27][CH:28]=1)[CH:25]=[C:24]([S:21]([N:18]1[CH2:19][CH2:20][N:15]([CH2:14][C:2]3([NH:1][C:36]([O:37][CH2:38][CH2:43][O:66][CH3:65])=[O:52])[CH2:7][CH2:6][N:5]([C:8]4[CH:9]=[CH:10][N:11]=[CH:12][CH:13]=4)[CH2:4][CH2:3]3)[C:16](=[O:35])[CH2:17]1)(=[O:22])=[O:23])[CH:33]=[CH:32]2

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 695505982-Methoxyethyl-4-nitrophenyl carbonateHCID 69550751HCID 69550751, compound

Product 1

HCID 695498594-(6-Chloronaphthalene-2-sulphonyl)-1-[4-(2-methoxyethoxycarbonylamino)-1-(4-pyridyl)-4-piperidylmethyl]-2-piperazinone

Procedure

A solution of 1-[4-amino-1-(4-pyridyl)-4-piperidylmethyl]-4-(6-chloronaphthalene-2-sulfonyl)-2-piperazinone (206 mg), 2-methoxyethyl-4-nitrophenyl carbonate (386 mg) and N-ethyldiisopropylamine (0.278 ml) in DMF (5 ml) was stirred at 60° C. overnight. The reaction mixture was concentrated under reduced pressure, ethyl acetate was added, the mixture was washed successively with a 10% aqueous sodium carbonate solution, an aqueous saturated sodium bicarbonate solution and an aqueous saturated sodium chloride solution, dried, and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate:10% aqueous ammonia-methanol=90:10→80:20), and crystallized from a mixed solution of acetone and ethyl acetate to obtain the colorless crystalline title compound (145 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, ethyl acetate
  2. additionwas added
  3. washthe mixture was washed successively with a 10% aqueous sodium carbonate solution
  4. dry with materialan aqueous saturated sodium bicarbonate solution and an aqueous saturated sodium chloride solution, dried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:10% aqueous ammonia-methanol=90:10→80:20)
  7. customcrystallized from a mixed solution of acetone and ethyl acetate

Sources & evidence

ORD record
ord-62ff12fc233e41609269162a94840a86
Source dataset
uspto-grants-2006_09
Patent number
US07109200B2

Reaction notes

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