4-Aminopyridine → HCID 25235900, compound

HRID 1360741Notes

Reaction equation

HRID 1360741 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=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:7]=[CH:6][N:5]=[CH:4][CH:3]=4)=[N:40][N:39]=3)[CH:34]=[CH:33][C:31]=2[N:32]=1

Participants

7

Reactant 4

HCID 17274-AminopyridineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 802641,1'-ThiocarbonyldiimidazoleHCID 577865852-(2,6-Dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid hydrazide

Product 1

HCID 25235900HCID 25235900, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

Combine 4-amino pyridine (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 (20-50% ACN/H2O+5 mM NH4OH) to afford the title compound: 1H NMR (400 MHz, DMSO-d6) δ ppm 7.63-7.68 (m, 1H) 7.71 (s, 1H) 7.73 (d, J=2.02 Hz, 1H) 7.76-7.97 (m, 4H) 8.05-8.27 (m, 1H) 8.58 (d, J=6.44 Hz, 2H) 13.34 (br. s., 1H); MS (m/z) 423.0 (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 (20-50% ACN/H2O+5 mM NH4OH)

Sources & evidence

ORD record
ord-2069450bea2f4fe5a5213895213992db
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Reaction notes

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