1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 25235255, compound

HRID 1360752Notes

Reaction equation

HRID 1360752 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.N1(C(N2C=CN=C2)=S)C=CN=[CH:10]1.[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:23]=1[C:29]1[NH:30][C:31]2[CH:37]=[C:36]([C:38]([NH:40][NH2:41])=[O:39])[CH:35]=[CH:34][C:32]=2[N:33]=1.CCN=C=NCCCN(C)C>CN(C=O)C.CCOC(C)=O>[Cl:8][C:5]1[N:4]=[CH:3][C:2]([NH:1][C:10]2[O:39][C:38]([C:36]3[CH:35]=[CH:34][C:32]4[N:33]=[C:29]([C:23]5[C:24]([Cl:28])=[CH:25][CH:26]=[CH:27][C:22]=5[Cl:21])[NH:30][C:31]=4[CH:37]=3)=[N:40][N:41]=2)=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 793055-Amino-2-chloropyridineHCID 802641,1'-ThiocarbonyldiimidazoleHCID 577865852-(2,6-Dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid hydrazide

Product 1

HCID 25235255HCID 25235255, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Combine 3-amino-6-chloro-pyridine (78 mg, 0.606 mmol) and di-imidazol-1-yl-methanethione (108 mg, 0.606 mmol) in DMF (1.5 mL) and stir for 4 hr. Add 2-(2,6-dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid hydrazide (150 mg, 0.466 mmol) and DMF (1 mL). Stir for 3 days. Add EDCI (179 mg, 0.932 mmol) and heat to 80° C. for 45 min. Upon cooling, dilute the reaction with EtOAc (50 mL) and extract with water (10 mL) and 1 N NaOH (10 mL). Combine the aqueous layers and allow to stand overnight. Evaporate the organic phase. Filter the combined aqueous layers and wash the collected solid with Et2O. Combine the solid with the residue from the organic phase and purify the material by reverse phase HPLC (20-65% ACN/H2O+5 mM NH4OH) to afford the title compound: 1H NMR (400 MHz, DMSO-d6) δ ppm 7.56 (d, J=8.72 Hz, 1H) 7.63-7.68 (m, 1H) 7.70 (s, 1H) 7.72 (d, J=2.02 Hz, 1H) 7.86 (br. s., 2H) 8.13 (br. s., 1H) 8.16 (dd, J=8.78, 2.97 Hz, 1H) 8.64 (d, J=2.91 Hz, 1H) 11.16 (s, 1H) 13.31 (br. s., 1H); MS m/z=458.9 (M+1).

Workup

  1. temperatureUpon cooling
  2. additiondilute
  3. extractionextract with water (10 mL) and 1 N NaOH (10 mL)
  4. waitto stand overnight
  5. customEvaporate the organic phase
  6. filtrationFilter the combined aqueous layers
  7. washwash the collected solid with Et2O
  8. custompurify the material by reverse phase HPLC (20-65% ACN/H2O+5 mM NH4OH)

Sources & evidence

ORD record
ord-d6c50b305a8044239fbc681995815815
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Reaction notes

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