1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 4-(5-{2-[3-(3-Chloro-phenyl)-[1,2,4]oxadiazol-5-yl]-propyl}-1-cyclopropyl-1H-imidazol-2-yl)-pyridine

HRID 732136Notes

Reaction equation

HRID 732136 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([NH:7][OH:8])=[NH:6].[CH:12]1([N:15]2[C:19]([CH2:20][CH:21]([CH3:25])[C:22](O)=O)=[CH:18][N:17]=[C:16]2[C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)[CH2:14][CH2:13]1.CCN=C=NCCCN(C)C.Cl.C1C=C2N=NN(O)C2=CC=1.O>O.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[N:6]=[C:22]([CH:21]([CH3:25])[CH2:20][C:19]3[N:15]([CH:12]4[CH2:14][CH2:13]4)[C:16]([C:26]4[CH:27]=[CH:28][N:29]=[CH:30][CH:31]=4)=[N:17][CH:18]=3)[O:8][N:7]=2)[CH:9]=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 578379903-(3-Cyclopropyl-2-pyridin-4-yl-3H-imidazol-4-yl)-2-methyl-propionic acidHCID 178513296HCID 178513296, compound

Product 1

HCID 115023474-(5-{2-[3-(3-Chloro-phenyl)-[1,2,4]oxadiazol-5-yl]-propyl}-1-cyclopropyl-1H-imidazol-2-yl)-pyridineYield 38.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

3-chloro-N-hydroxy-benzamidine (486 mg, 2.85 mmol), 3-(3-cyclopropyl-2-pyridin-4-yl-3H-imidazol-4-yl)-2-methyl-propionic acid (702 mg, 2.59 mmol), EDCl (546 mg, 2.85 mmol) and HOBt hydrate (385 mg, 2.85 mmol) were mixed with DMF (20 ml) and stirred o.n. at r.t. The reaction was diluted with water and extracted with EA. The combined organic phase was successively washed with sat. aq. sodium bicarbonate, brine, dried (Na2SO4), filtered and concentrated in-vacuo. The residue was heated in DMF (10 ml) at 120° C. for 2 h. The reaction mixture was cooled to r.t., diluted with EA (50 ml), successively washed with water and brine, dried (Na2SO4), filtered and concentrated in-vacuo. The crude was purified via column chromatography using 2% MeOH in DCM to isolate the title compound (404 mg). 1H-NMR: 8.69 (dd, 2H), 8.09 (m, 1H), 7.96 (d, 1H), 7.67 (dd, 2H), 7.46 (m, 2H), 6.94 (s, 1H), 3.66 (m, 1H), 3.48 (m, 1H), 3.31 (m, 1H), 3.16 (m, 1H), 1.59 (d, 3H), 1.19 (m, 2H), 0.72 (m, 2H).

Workup

  1. customat r.t
  2. extractionextracted with EA
  3. washThe combined organic phase was successively washed with sat. aq. sodium bicarbonate, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in-vacuo
  7. temperatureThe reaction mixture was cooled to r.t.
  8. additiondiluted with EA (50 ml)
  9. washsuccessively washed with water and brine
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. concentrationconcentrated in-vacuo
  13. customThe crude was purified via column chromatography

Sources & evidence

ORD record
ord-c608c50c16c54b4f81b0869222e78ea9
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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