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Diethyl Ether → Methyl 3-[5-amino-4-(cyclohexylcarbamoyl)pyrazol-1-yl]benzoate

HRID 1799394
Notes
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Reaction equation

HRID 1799394 reaction equation
[C:1]([C:3](=[CH:13]OCC)[C:4]([NH:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:5])#[N:2].Cl.[NH:18]([C:20]1[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=1)[C:23]([O:25][CH3:26])=[O:24])[NH2:19].CCN(C(C)C)C(C)C.CCOCC>C(O)C>[NH2:2][C:1]1[N:18]([C:20]2[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=2)[C:23]([O:25][CH3:26])=[O:24])[N:19]=[CH:13][C:3]=1[C:4](=[O:5])[NH:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 81531DiisopropylethylamineHCID 23285088Methyl 3-hydrazinylbenzoate hydrochlorideHCID 670194772-cyano-N-cyclohexyl-3-ethoxy-prop-2-enamide2×

Product 1

HCID 57437899Methyl 3-[5-amino-4-(cyclohexylcarbamoyl)pyrazol-1-yl]benzoateYield 47.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

2-cyano-N-cyclohexyl-3-ethoxy-prop-2-enamide (Intermediate #17) (605 mg, 2.73 mmol) and methyl 3-hydrazinylbenzoate hydrochloride (552 mg, 2.73 mmol) were suspended in ethanol (20 mL). DIPEA (352 mg, 2.73 mmol) was added and the mixture heated to 70° C. for 1 h. The reaction mixture was cooled to ambient and concentrated to a small volume. Water (50 mL) was added and the resulting solid recovered by filtration, redissolved in ethyl acetate (50 mL), dried (MgSO4) and evaporated to give a brown solid which was slurried with ether and recovered by filtration to give the title compound as light brown solid (443 mg, 47%).

Workup

  1. temperatureThe reaction mixture was cooled to ambient and
  2. concentrationconcentrated to a small volume
  3. additionWater (50 mL) was added
  4. filtrationthe resulting solid recovered by filtration
  5. dissolutionredissolved in ethyl acetate (50 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customto give a brown solid which
  9. filtrationrecovered by filtration

Sources & evidence

ORD record
ord-65af74981ce94f9aaf13a1f9821d0720
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08344016B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes