1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 25235948, compound

HRID 1360751Notes

Reaction equation

HRID 1360751 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]([CH3:8])=[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: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]3[O:39][C:10]([NH:1][C:2]4[CH:3]=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=4)=[N:41][N:40]=3)[CH:35]=[CH:34][C:32]=2[N:33]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 802641,1'-ThiocarbonyldiimidazoleHCID 2433135-Amino-2-methylpyridineHCID 577865852-(2,6-Dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid hydrazide

Product 1

HCID 25235948HCID 25235948, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
4 °C

Procedure

Combine 3-amino-6-methyl-pyridine (66 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. Filter the combined aqueous layers and wash the collected solid with Et2O. Suspend the solid in boiling toluene/EtOAc. Allow the suspension to cool to 4° C. and collect the solid. Wash with Et2O. Purify the solid by reverse phase HPLC (20-65% ACN/H2O+5 mM NH4OH) to afford the title compound: 1H NMR (400 MHz, DMSO-d6) δ ppm 2.46 (s, 3H) 7.33 (d, J=8.34 Hz, 1H) 7.64-7.68 (m, 1H) 7.71 (s, 1H) 7.73 (d, J=2.02 Hz, 1H) 7.86 (br. s., 2H) 8.04 (dd, J=8.40, 2.46 Hz, 1H) 8.13 (br. s., 1H) 8.70 (d, J=2.53 Hz, 1H) 10.88 (br. s., 1H); MS m/z=437.0 (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. filtrationFilter the combined aqueous layers
  6. washwash the collected solid with Et2O
  7. customcollect the solid
  8. washWash with Et2O
  9. customPurify the solid by reverse phase HPLC (20-65% ACN/H2O+5 mM NH4OH)

Sources & evidence

ORD record
ord-4513b414e41942789826b59757b7ff7b
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Reaction notes

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