Ethyl Acetate → HCID 69550120, compound

HRID 2214821Notes

Reaction equation

HRID 2214821 reaction equation
Cl.Cl.[NH2:3][C:4]1([CH2:16][N:17]2[CH2:22][CH2:21][N:20]([S:23]([C:26]3[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[C:31]([Cl:36])[CH:32]=4)[CH:27]=3)(=[O:25])=[O:24])[CH2:19][C:18]2=[O:37])[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[CH2:6][CH2:5]1.[CH2:38]([O:41][C:42](OC1C=CC([N+]([O-])=O)=CC=1)=[O:43])[CH2:39][CH3:40].C(N(C(C)C)C(C)C)C.C(OCC)(=O)C>CN(C=O)C>[Cl:36][C:31]1[CH:32]=[C:33]2[C:28](=[CH:29][CH:30]=1)[CH:27]=[C:26]([S:23]([N:20]1[CH2:21][CH2:22][N:17]([CH2:16][C:4]3([NH:3][C:42]([O:41][CH2:38][CH2:39][CH3:40])=[O:43])[CH2:9][CH2:8][N:7]([C:10]4[CH:11]=[CH:12][N:13]=[CH:14][CH:15]=4)[CH2:6][CH2:5]3)[C:18](=[O:37])[CH2:19]1)(=[O:24])=[O:25])[CH:35]=[CH:34]2

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 544839324-Nitrophenyl propyl carbonateHCID 69550750HCID 69550750, compound

Product 1

HCID 69550120HCID 69550120, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-[4-amino-1-(4-pyridyl)-4-piperidylmethyl]-4-(6-chloronaphthalene-2-sulfonyl)-2-piperazinone dihydrochloride (235 mg), O-propoxycarbonyl-4-nitrophenol (270 mg) and N-ethyldiisopropylamine (0.348 ml) in DMF (5 ml) was stirred at 80° C. overnight. To the reaction solution was added ethyl acetate, 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-containing methanol=90:10→80:20), and crystallized from a mixed solution of acetone and ethyl acetate to obtain the pale brown crystalline title compound (114 mg).

Workup

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

Sources & evidence

ORD record
ord-0ad99562e80840ca9ad1573722631a80
Source dataset
uspto-grants-2006_09
Patent number
US07109200B2

Reaction notes

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