1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 25235254, compound

HRID 1360753Notes

Reaction equation

HRID 1360753 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]([O:8][CH3:9])=[CH:6][CH:7]=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.C([O-])(O)=O.[Na+].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:1][C:2]4[CH:3]=[N:4][C:5]([O:8][CH3:9])=[CH:6][CH:7]=4)=[N:42][N:41]=3)[CH:36]=[CH:35][C:33]=2[N:34]=1

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 802641,1'-ThiocarbonyldiimidazoleHCID 811216-Methoxy-3-pyridinylamineHCID 577865852-(2,6-Dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid hydrazide

Product 1

HCID 25235254HCID 25235254, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
80 °C

Procedure

Combine 3-amino-6-methoxy-pyridine (64 uL, 0.606 mmol) and di-imidazol-1-yl-methanethione (108 mg, 0.606 mmol) in DMF (1.5 mL) and stir for 3 hr. Add 2-(2,6-dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid hydrazide (150 mg, 0.466 mmol) and DMF (1 mL). Heat to 80° C. for 1 hr. Add EDCI (179 mg, 0.932 mmol) and heat to 80° C. for 1 hr. Upon cooling, dilute the reaction with EtOAc (50 mL) and extract with water (10 mL). Dry the organic phase over Na2SO4 and concentrate. Triturate the concentrate with hot EtOAc/toluene to obtain a white solid. Suspend the solid in saturated NaHCO3 and stir vigorously. Collect the solid and purify by silica gel chromatography (10-100% EtOAc/HEP, 0-50% MeOH/DCM) to afford the title compound as a white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 3.84 (s, 3H) 6.89 (d, J=8.84 Hz, 1H) 7.62-7.67 (m, 1H) 7.70 (s, 1H) 7.72 (d, J=1.64 Hz, 1H) 7.76 (tautomer, d, J=8.46 Hz, 1H) 7.81 (tautomer, dd, J=8.46, 1.26 Hz, 1H) 7.85-7.92 (mixture of tautomers, m, 1H) 7.96-8.01 (m, 1H) 8.03 (tautomer, s, 1H) 8.16 (tautomer, s, 1H) 8.44 (s, 1H) 10.63 (s, 1H) 13.28 (s, 1H); MS m/z=453.0 (M+1).

Workup

  1. temperatureUpon cooling
  2. additiondilute
  3. extractionextract with water (10 mL)
  4. dry with materialDry the organic phase over Na2SO4
  5. concentrationconcentrate
  6. customTriturate the
  7. concentrationconcentrate with hot EtOAc/toluene
  8. customto obtain a white solid
  9. customCollect the solid
  10. custompurify by silica gel chromatography (10-100% EtOAc/HEP, 0-50% MeOH/DCM)

Sources & evidence

ORD record
ord-d00b971b2dd04976b3b75080617ca825
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Reaction notes

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