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Sodium Sulfate → ethyl (RS)-(4-cyano-phenylamino)-[3-ethyl-5-(1-methyl-piperidin-4-ylamino)-phenyl]-acetate

HRID 1016789
Notes
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Reaction equation

HRID 1016789 reaction equation
[O-]S([O-])(=O)=O.[Na+].[Na+].[NH2:8][C:9]1[CH:10]=[C:11]([CH:17]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=2)[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:12]=[C:13]([CH2:15][CH3:16])[CH:14]=1.[CH3:32][N:33]1[CH2:38][CH2:37][C:36](=O)[CH2:35][CH2:34]1.C([O-])(O)=O.[Na+]>C(O)(=O)C>[C:30]([C:27]1[CH:28]=[CH:29][C:24]([NH:23][CH:17]([C:11]2[CH:10]=[C:9]([NH:8][CH:36]3[CH2:37][CH2:38][N:33]([CH3:32])[CH2:34][CH2:35]3)[CH:14]=[C:13]([CH2:15][CH3:16])[CH:12]=2)[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:25][CH:26]=1)#[N:31]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 24436Sodium SulfateHCID 740491-Methyl-4-piperidoneHCID 516892Sodium BicarbonateHCID 86583558ethyl (RS)-(3-amino-5-ethyl-phenyl)-(4-cyano-phenylamino)-acetate

Product 1

HCID 86583561ethyl (RS)-(4-cyano-phenylamino)-[3-ethyl-5-(1-methyl-piperidin-4-ylamino)-phenyl]-acetateYield 89%

Reagents, catalysts & solvents

1
HCID 176Acetic AcidSolvent

Procedure

Na2SO4 (1.09 g, 7.7 mmol) was added to a solution of the ethyl (RS)-(3-amino-5-ethyl-phenyl)-(4-cyano-phenylamino)-acetate (250 mg, 0.77 mmol) obtained in Example 223.4 and 1-methyl-4-piperidone (174 mg, 1.54 mmol) in acetic acid (5 ml) and the mixture was stirred for 15 min. at room temperature. The mixture was subsequently cooled to 0° C. and NaHB(OAc)3 (489 mg, 2.31 mmol) was slowly added portionwise. After 30 min. a saturated solution of NaHCO3 was added and the mixture was extracted with EtOAc. The organic phase was dried and filtered, and the filtrate was concentrated. The residue was purified by chromatography (SiO2, CH2Cl2/MeOH 9:1). There were obtained 287 mg (89%) of ethyl (RS)-(4-cyano-phenylamino)-[3-ethyl-5-(1-methyl-piperidin-4-ylamino)-phenyl]-acetate as a yellowish solid; MS: 421 ([M+H]+).

Workup

  1. temperatureThe mixture was subsequently cooled to 0° C.
  2. extractionthe mixture was extracted with EtOAc
  3. customThe organic phase was dried
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by chromatography (SiO2, CH2Cl2/MeOH 9:1)

Sources & evidence

ORD record
ord-83334186f7e74a61b802835110dc301a
Source dataset
uspto-grants-2002_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06476264B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes