1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 25235303, compound

HRID 1360758Notes

Reaction equation

HRID 1360758 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8].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][CH:5]=[CH:6][C:7]=4[CH3:8])=[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 1379353-Amino-4-picolineHCID 577865852-(2,6-Dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid hydrazide

Product 1

HCID 25235303HCID 25235303, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Combine 3-amino-4-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 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 (30-45% ACN/H2O+5 mM NH4OH) to afford the title compound as a light yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 2.35 (s, 3H) 7.30 (d, J=4.80 Hz, 1H) 7.62-7.68 (m, 1H) 7.72 (d, J=2.02 Hz, 1H) 7.70 (s, 1H) 7.83 (br. s., 2H) 7.98-8.19 (m, 1H) 8.24 (d, J=4.80 Hz, 1H) 8.98 (s, 1H) 9.95 (br. s., 1H) 13.28 (br. s., 1H); MS m/z=436.9 (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 (30-45% ACN/H2O+5 mM NH4OH)

Sources & evidence

ORD record
ord-70c46147a6c744fcb46208d4654c47d0
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Reaction notes

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