Acetic Acid → HCID 86732051, compound

HRID 1498791Notes

Reaction equation

HRID 1498791 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[N:13]=[N:12][CH:11]=[C:10]([C@@H:14]3[CH2:16][C@H:15]3[CH:17]=O)[CH:9]=2)[N:3]=1.[CH3:19][NH:20][C:21]1[C:22]([NH2:27])=[CH:23][CH:24]=[CH:25][CH:26]=1.CC(O)=O.N>C(O)C.[O-]S([O-])(=O)=O.[Cu+2]>[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[N:13]=[N:12][CH:11]=[C:10]([C@@H:14]3[CH2:16][C@H:15]3[C:17]3[N:20]([CH3:19])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[N:27]=3)[CH:9]=2)[N:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 222AmmoniaHCID 78498N-Methyl-o-phenylenediamineHCID 86732052HCID 86732052, compound

Product 1

HCID 86732051HCID 86732051, compound

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 702EthanolSolvent2×

Procedure

To a solution of trans-2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)pyridazin-4-yl)cyclopropanecarbaldehyde (23-6, 70 mg, 0.29 mmol, 1.0 eq.) and N1-methylbenzene-1,2-diamine (42 mg, 0.35 mmol, 1.2 eq.) in ethanol (1.5 mL) was added anhydrous CuSO4 (56 mg, 0.35 mmol, 1.2 eq.) and AcOH (21 mg, 0.35 mmol, 1.2 eq.). The mixture was stirred at room temperature for 4 hours then basified with 2 M NH3 in ethanol (1.0 mL). The resulting mixture was filtered and the filtrate was concentrated. The residue was purified by silica gel column chromatography (70% acetone in hexanes) to afford trans-2-(2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)pyridazin-4-yl)cyclopropyl)-1-methyl-1H-benzo[d]imidazole (23-7) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 9.07 (d, 1H, J=2.1 Hz), 7.80 (d, 1H, J=2.1 Hz), 7.75-7.66 (m, 1H), 7.35-7.22 (m, 3H), 3.84 (s, 3H), 2.96 (s, 3H), 2.86 (m, 1H), 2.52 (m, 1H), 2.44 (s, 3H), 2.18 (m, 1H), 1.83 (m, 1H). LRMS m/z (M+H) 346.0 found, 346.4 required.

Workup

  1. filtrationThe resulting mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel column chromatography (70% acetone in hexanes)

Sources & evidence

ORD record
ord-48520d525a504e12a4c1fbaf1b097c72
Source dataset
uspto-grants-2015_12
Patent number
US09200001B2

Reaction notes

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