Acetic Acid → HCID 86732056, compound

HRID 1498794Notes

Reaction equation

HRID 1498794 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[CH:13]=[C:12]([CH3:14])[N:11]=[C:10]([C@@H:15]3[CH2:17][C@H:16]3[CH:18]=O)[CH:9]=2)[N:3]=1.[CH3:20][NH:21][C:22]1[C:23]([NH2:28])=[CH:24][CH:25]=[CH:26][CH:27]=1.CC(O)=O.C([O-])(O)=O.[Na+]>C(O)C.S([O-])([O-])(=O)=O.[Cu+2]>[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[CH:13]=[C:12]([CH3:14])[N:11]=[C:10]([C@@H:15]3[CH2:17][C@H:16]3[C:18]3[N:21]([CH3:20])[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[N:28]=3)[CH:9]=2)[N:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 78498N-Methyl-o-phenylenediamineHCID 516892Sodium BicarbonateHCID 86732057HCID 86732057, compound

Product 1

HCID 86732056HCID 86732056, compound

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 702EthanolSolvent

Procedure

A mixture of trans-2-(4-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-6-methylpyridin-2-yl)cyclopropanecarbaldehyde (24-7, 74 mg, 0.289 mmol), N1-methylbenzene-1,2-diamine (35 mg, 0.289 mmol), copper(II) sulfate (51 mg, 0.318 mmol), and AcOH (35 mg, 0.578 mmol) in ethanol (3 mL) was stirred at room temperature overnight. NaHCO3 (100 mg) was added and the mixture was stirred for 5 minutes and filtered. The filtrate was concentrated and the residue was purified by silica gel column chromatography (10% methanol in DCM) and reverse phase chromatography (10-100% acetonitrile in water) to afford trans-2-(2-(4-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-6-methylpyridin-2-yl)cyclopropyl)-1-methyl-1H-benzo[d]imidazole (24-8) as a light yellow oil. 1H NMR (300 MHz, CDCl3) 57.73-7.65 (m, 1H), 7.33-7.18 (m, 4H), 7.14 (d, 1H, J=1.7 Hz), 3.83 (s, 3H), 2.88-2.75 (m, 2H), 2.60 (s, 3H), 2.59 (s, 3H), 2.41 (s, 3H), 1.98-1.87 (m, 2H). LRMS m/z (M+H) 359 found, 359 required.

Workup

  1. stirringthe mixture was stirred for 5 minutes
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by silica gel column chromatography (10% methanol in DCM)

Sources & evidence

ORD record
ord-118df8725aa94186a30cac0adf2b471d
Source dataset
uspto-grants-2015_12
Patent number
US09200001B2

Reaction notes

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