3-Aminopyridine → {5-[2-(2,6-Dichloro-phenyl)-3H-benzoimidazol-5-yl]-[1,3,4]oxadiazol-2-yl}-pyridin-3-yl-amine

HRID 1513239Notes

Reaction equation

HRID 1513239 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.N1(C(N2C=CN=C2)=S)C=CN=[CH:9]1.[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:22]=1[C:28]1[NH:29][C:30]2[CH:36]=[C:35]([C:37]([NH:39][NH2:40])=[O:38])[CH:34]=[CH:33][C:31]=2[N:32]=1.CCN=C=NCCCN(C)C>CN(C=O)C.O>[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:22]=1[C:28]1[NH:29][C:30]2[CH:36]=[C:35]([C:37]3[O:38][C:9]([NH:1][C:2]4[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=4)=[N:40][N:39]=3)[CH:34]=[CH:33][C:31]=2[N:32]=1

Participants

7

Reactant 4

HCID 100093-AminopyridineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 802641,1'-ThiocarbonyldiimidazoleHCID 577865852-(2,6-Dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid hydrazide

Product 1

HCID 25235903{5-[2-(2,6-Dichloro-phenyl)-3H-benzoimidazol-5-yl]-[1,3,4]oxadiazol-2-yl}-pyridin-3-yl-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

Combine 3-aminopryidine (30 mg, 0.312 mmol) and di-imidazol-1-yl -methanethione (56 mg, 0.312 mmol) in DMF (0.3 mL) and stir for 2 days. Add 2-(2,6-dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid hydrazide (77 mg, 0.240 mmol) and dilute with DMF (1.5 mL). Heat the reaction to 80° C. for 1 hr. Add EDCI (92 mg, 0.480 mmol) and heat for 1 hr at 80° C. Allow reaction to cool to room temp and dilute the reaction with water. Collect the resulting precipitate by filtration. Purify the solid by reverse-phase HPLC (25-65% ACN/H2O+5 mM NH4OH) to afford the title compound: 1H NMR (400 MHz, DMSO-d6) δ ppm 7.44 (dd, J=8.34, 4.80 Hz, 1 H) 7.63-7.67 (m, 1H) 7.70 (s, 1 H) 7.72 (d, J=1.77 Hz, 1 H) 7.87 (br. s., 2 H) 8.13 (ddd, J=8.40, 2.59, 1.39 Hz, 2 H) 8.25 (dd, J=4.80, 1.26 Hz, 1 H) 8.80 (d, J=2.53 Hz, 1 H) 10.98 (s, 1 H) 13.30 (br. s., 1H); MS (m/z) 423.1 (M+1).

Workup

  1. temperatureHeat
  2. customthe reaction to 80° C. for 1 hr
  3. customreaction
  4. additiondilute
  5. customCollect the resulting precipitate
  6. filtrationby filtration
  7. customPurify the solid by reverse-phase HPLC (25-65% ACN/H2O+5 mM NH4OH)

Sources & evidence

ORD record
ord-f172ce5fe80249e39a481109448b475a
Source dataset
uspto-grants-2012_07
Patent number
US08217065B2

Reaction notes

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