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 732136노트

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HRID 732136 반응식
[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

참가 물질

7

반응물 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, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
120 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c608c50c16c54b4f81b0869222e78ea9
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585881B2

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