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Dimethyl acetylsuccinate → HCID 178499487, compound

HRID 574338
Notes
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Reaction equation

HRID 574338 reaction equation
[Br:1][C:2]1[CH:6]=[C:5]([NH2:7])[NH:4][N:3]=1.[C:8]([CH:11]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[C:12](OC)=[O:13])(=O)[CH3:9]>C1(C)C(C)=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[CH:6]=[C:5]2[N:7]=[C:8]([CH3:9])[C:11]([CH2:16][C:17]([O:19][CH3:20])=[O:18])=[C:12]([OH:13])[N:4]2[N:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 112039Dimethyl acetylsuccinateHCID 178507227HCID 178507227, compound

Product 1

HCID 178499487HCID 178499487, compoundYield 54.2%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 7237O-XyleneSolvent

Procedure

To a solution of 3-bromo-1H-pyrazol-5-amine (0.2 g, 1.235 mmol) and dimethyl 2-acetylsuccinate (0.697 g, 3.70 mmol) in xylene (10 mL) was added p-toluenesulfonic acid monohydrate (2 mg, 10.51 μmol). The reaction mixture was heated at reflux under a Dean-Stark trap for 8 h. The solid was filtered and washed with hexanes to afford the title compound (0.201 g, 54.2%). 1H NMR (400 MHz, MeOD) δ 2.37 (3H, s), 3.65 (2H, s), 3.71 (3H, s), 6.20 (1H, s).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux under a Dean-Stark trap for 8 h
  3. filtrationThe solid was filtered
  4. washwashed with hexanes

Sources & evidence

ORD record
ord-93d4d0baca6349ee913cfc4bd17428b9
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09034882B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes