1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 25235304, compound

HRID 1513255Notes

Reaction equation

HRID 1513255 reaction equation
[CH3:1][O:2][C:3]1[C:8]([NH2:9])=[CH:7][CH:6]=[CH:5][N:4]=1.N1(C(N2C=CN=C2)=S)C=CN=[CH:11]1.[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:24]=1[C:30]1[NH:31][C:32]2[CH:38]=[C:37]([C:39]([NH:41][NH2:42])=[O:40])[CH:36]=[CH:35][C:33]=2[N:34]=1.CCN=C=NCCCN(C)C>CN(C=O)C.CCOC(C)=O>[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:24]=1[C:30]1[NH:31][C:32]2[CH:38]=[C:37]([C:39]3[O:40][C:11]([NH:9][C:8]4[C:3]([O:2][CH3:1])=[N:4][CH:5]=[CH:6][CH:7]=4)=[N:42][N:41]=3)[CH:36]=[CH:35][C:33]=2[N:34]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 802641,1'-ThiocarbonyldiimidazoleHCID 27374883-Amino-2-methoxypyridineHCID 577865852-(2,6-Dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid hydrazide

Product 1

HCID 25235304HCID 25235304, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Combine 2-methoxy-3-amino-pyridine (75 mg, 0.606 mmol) and di -imidazol-1-yl-methanethione (108 mg, 0.606 mmol) in DMF (1.5 mL) and stir for 7.5 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 1 hr. Upon cooling, dilute the reaction with EtOAc (75 mL) and extract with water (15 mL). Dry the organic phase over Na2SO4 and evaporate the solvent. Purify the residue by reverse phase HPLC (35-50% ACN/H2O+5 mM NH4OH) to afford the title compound as a light tan solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 3.98 (s, 3 H) 7.07 (dd, J=7.77, 4.99 Hz, 1 H) 7.62-7.68 (m, 1 H) 7.72 (d, J=1.89 Hz, 1 H) 7.70 (s, 1 H) 7.74-7.92 (m, 3 H) 8.00-8.23 (m, 1 H) 8.42 (dd, J=7.83, 1.64 Hz, 1 H) 10.12 (br. s., 1 H) 13.30 (br. s., 1 H); MS m/z=452.9 (M+1).

Workup

  1. temperatureUpon cooling
  2. additiondilute
  3. extractionextract with water (15 mL)
  4. dry with materialDry the organic phase over Na2SO4
  5. customevaporate the solvent
  6. customPurify the residue by reverse phase HPLC (35-50% ACN/H2O+5 mM NH4OH)

Sources & evidence

ORD record
ord-37291c8c235b48f1b073c8bd82838050
Source dataset
uspto-grants-2012_07
Patent number
US08217065B2

Reaction notes

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