1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Adamantan-1-yl-{5-[2-(2,6-dichloro-phenyl)-3H-benzoimidazol-5-yl]-[1,3,4]oxadiazol-2-yl}-amine

HRID 1513240Notes

Reaction equation

HRID 1513240 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[NH:10][C:11]2[CH:17]=[C:16]([C:18]([NH:20][NH2:21])=[O:19])[CH:15]=[CH:14][C:12]=2[N:13]=1.[N:22]([C:25]12[CH2:34][CH:29]3[CH2:30][CH:31]([CH2:33][CH:27]([CH2:28]3)[CH2:26]1)[CH2:32]2)=[C:23]=S.CCN=C=NCCCN(C)C>CN(C=O)C.O>[C:25]12([NH:22][C:23]3[O:19][C:18]([C:16]4[CH:15]=[CH:14][C:12]5[N:13]=[C:9]([C:3]6[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=6[Cl:1])[NH:10][C:11]=5[CH:17]=4)=[N:20][N:21]=3)[CH2:32][CH:31]3[CH2:30][CH:29]([CH2:28][CH:27]([CH2:33]3)[CH2:26]1)[CH2:34]2

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 107279Adamantyl isothiocyanateHCID 577865852-(2,6-Dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid hydrazide

Product 1

HCID 25235902Adamantan-1-yl-{5-[2-(2,6-dichloro-phenyl)-3H-benzoimidazol-5-yl]-[1,3,4]oxadiazol-2-yl}-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Combine 2-(2,6-dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid hydrazide (100 mg, 0.310 mmol) and 1-isothiocyanato-adamantane (78 mg, 0.403 mmol) in DMF (2 mL) and heat to 70° C. for 1 hr. Add EDCI (119 mg, 0.620 mmol) and heat the reaction for 1 hr. Allow the reaction to cool to room temp and dilute with water (10 mL). Collect the resulting precipitate by filtration and purify the solid by reverse-phase HPLC (35-65% ACN/H2O+5 mM NH4OH) to afford the title compound as a white solid: 1H NMR (400 MHz, MeOD) δ ppm 1.74-1.82 (m, 6 H) 2.12 (s, 6 H) 2.15 (br. s., 3 H) 7.55-7.63 (m, 3 H) 7.76 (br. s., 1 H) 7.93 (br. s., 1 H) 8.18 (br. s., 1 H); MS (m/z) 480.1 (M+1).

Workup

  1. customthe reaction for 1 hr
  2. customthe reaction
  3. customCollect the resulting precipitate
  4. filtrationby filtration
  5. custompurify the solid by reverse-phase HPLC (35-65% ACN/H2O+5 mM NH4OH)

Sources & evidence

ORD record
ord-ee13faa6c5fa45ff9f8a9bc198f869c9
Source dataset
uspto-grants-2012_07
Patent number
US08217065B2

Reaction notes

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