1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 25235258, compound

HRID 1513252Notes

Reaction equation

HRID 1513252 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:7]=1.N1(C(N2C=CN=C2)=S)C=CN=[CH:13]1.[Cl:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[C:26]=1[C:32]1[NH:33][C:34]2[CH:40]=[C:39]([C:41]([NH:43][NH2:44])=[O:42])[CH:38]=[CH:37][C:35]=2[N:36]=1.CCN=C=NCCCN(C)C>CN(C=O)C.CCOC(C)=O>[Cl:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[C:26]=1[C:32]1[NH:33][C:34]2[CH:40]=[C:39]([C:41]3[O:42][C:13]([NH:1][C:2]4[CH:3]=[N:4][C:5]([C:8]([F:11])([F:9])[F:10])=[CH:6][CH:7]=4)=[N:44][N:43]=3)[CH:38]=[CH:37][C:35]=2[N:36]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 802641,1'-ThiocarbonyldiimidazoleHCID 27377445-Amino-2-(trifluoromethyl)pyridineHCID 577865852-(2,6-Dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid hydrazide

Product 1

HCID 25235258HCID 25235258, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Combine 3-amino-6-trifluoromethyl-pyridine (98 mg, 0.606 mmol) and di -imidazol-1-yl-methanethione (108 mg, 0.606 mmol) in DMF (1.5 mL) and stir overnight. Add 2-(2,6-dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid hydrazide (150 mg, 0.466 mmol) and DMF (1 mL). Stir for 6.5 hr. 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 silica gel chromatography (3-6% MeOH/DCM) to afford the title compound as an off white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 7.62-7.68 (m, 1 H) 7.71 (d, J=1.01 Hz, 1 H) 7.73 (t, J=1.77 Hz, 1 H) 7.78 (tautomer, d, J=8.59 Hz, 1 H) 7.82-7.87 (tautomer, m, 1 H) 7.90-7.94 (m, 1 H) 7.96 (d, J=8.72 Hz, 1 H) 8.08 (tautomer, d, J=0.88 Hz, 1 H) 8.21 (tautomer, s, 1 H) 8.38 (d, J=8.59 Hz, 1 H) 8.90 (d, J=2.27 Hz, 1 H) 11.51 (s, 1 H) 13.32 (d, J=2.91 Hz, 1 H); MS m/z=490.9 (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 silica gel chromatography (3-6% MeOH/DCM)

Sources & evidence

ORD record
ord-2e3ee39f3f394b15b76af72286c1765a
Source dataset
uspto-grants-2012_07
Patent number
US08217065B2

Reaction notes

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