Acetonitrile → Methyl 5-({[4-(2-{3-[(aminocarbonyl)amino]phenyl}ethyl)-1-piperidyl]carbonyl}oxy)nicotinate

HRID 2074255Notes

Reaction equation

HRID 2074255 reaction equation
[N+](C1C=CC(O[C:9]([O:11][C:12]2[CH:13]=[N:14][CH:15]=[C:16]([CH:21]=2)[C:17]([O:19][CH3:20])=[O:18])=[O:10])=CC=1)([O-])=O.C(#N)C.Cl.[NH:28]1[CH2:33][CH2:32][CH:31]([CH2:34][CH2:35][C:36]2[CH:37]=[C:38]([NH:42][C:43]([NH2:45])=[O:44])[CH:39]=[CH:40][CH:41]=2)[CH2:30][CH2:29]1>CCOC(C)=O>[NH2:45][C:43]([NH:42][C:38]1[CH:37]=[C:36]([CH2:35][CH2:34][CH:31]2[CH2:32][CH2:33][N:28]([C:9]([O:11][C:12]3[CH:13]=[N:14][CH:15]=[C:16]([CH:21]=3)[C:17]([O:19][CH3:20])=[O:18])=[O:10])[CH2:29][CH2:30]2)[CH:41]=[CH:40][CH:39]=1)=[O:44]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 57421835Methyl 5-{[(4-nitrophenoxy)carbonyl]oxy}nicotinateHCID 574218381-{3-[2-(4-Piperidinyl)ethyl]phenyl}urea hydrochloride

Product 1

HCID 57507768Methyl 5-({[4-(2-{3-[(aminocarbonyl)amino]phenyl}ethyl)-1-piperidyl]carbonyl}oxy)nicotinateYield 65.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Methyl 5-{[(4-nitrophenoxy)carbonyl]oxy}nicotinate (228 mg) was added to an acetonitrile (5 ml) solution of 1-{3-[2-(4-piperidinyl)ethyl]phenyl}urea hydrochloride (185 mg) and TEA (0.2 ml), followed by stirring overnight at room temperature. The reaction liquid was diluted with EtOAc, washed with aqueous saturated sodium hydrogencarbonate solution and saturated brine in that order, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (eluent: chloroform:methanol=10:1 (v/v)) to obtain methyl 5-({[4-(2-{3-[(aminocarbonyl)amino]phenyl}ethyl)-1-piperidyl]carbonyl}oxy)nicotinate (183 mg).

Workup

  1. customThe reaction liquid
  2. washwashed with aqueous saturated sodium hydrogencarbonate solution and saturated brine in that order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe resulting residue was purified by silica gel column chromatography (eluent: chloroform:methanol=10:1 (v/v))

Sources & evidence

ORD record
ord-876295eccc4c44bdab66445322f279dc
Source dataset
uspto-grants-2011_04
Patent number
US07919494B2

Reaction notes

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