Ethyl isothiocyanate → 6-(2-(2,4-Difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-N-ethyl-[1,2,4]triazolo[4,3-b]pyridazin-3-amine

HRID 1930020노트

반응식

HRID 1930020 반응식
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]2[CH2:24][CH2:23][CH2:22][N:12]2[C:13]=1[C:14]1[N:15]=[N:16][C:17]([NH:20][NH2:21])=[CH:18][CH:19]=1.[N:25]([CH2:28][CH3:29])=[C:26]=S>CN(C1C=CN=CC=1)C.CCO>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]2[CH2:24][CH2:23][CH2:22][N:12]2[C:13]=1[C:14]1[CH:19]=[CH:18][C:17]2[N:16]([C:26]([NH:25][CH2:28][CH3:29])=[N:21][N:20]=2)[N:15]=1

참가 물질

5

반응물 2

HCID 10966Ethyl isothiocyanateHCID 579298742-(2,4-Difluorophenyl)-3-(6-hydrazinylpyridazin-3-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole

생성물 1

HCID 579299416-(2-(2,4-Difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-N-ethyl-[1,2,4]triazolo[4,3-b]pyridazin-3-amine수율 17.2%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 702Ethanol용매

반응 조건

온도
75 °C

실험 절차

2-(2,4-Difluorophenyl)-3-(6-hydrazinylpyridazin-3-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole (0.200 g, 0.609 mmol, Example #35, Step E) and isothiocyanatoethane (0.085 g, 0.975 mmol) were added to EtOH (3 mL). The suspension was heated to about 75° C. for about 3 h. DMAP (0.138 g, 0.670 mmol) was added and the solution was heated in a CEM® microwave at about 150° C. for about 10 min (250 psi maximum pressure, 10 min ramp, 300 max watts). Solvent was removed in vacuo and the material was purified by flash chromatography using MeOH/DCM (0-6% gradient) and then further purified by RP-HPLC (Table 1, Method m). The ACN was removed and the resulting precipitate was collected to afford the title compound (0.040 g, 17%): LC/MS (Table 1, Method g) Rt=1.77 min; MS m/z: 382.2 (M+1)+.

후처리

  1. temperaturethe solution was heated in a CEM® microwave at about 150° C. for about 10 min (250 psi maximum pressure, 10 min ramp, 300 max watts)
  2. customSolvent was removed in vacuo
  3. customthe material was purified by flash chromatography
  4. customfurther purified by RP-HPLC (Table 1, Method m)
  5. customThe ACN was removed
  6. customthe resulting precipitate was collected

출처 및 근거

ORD 기록
ord-ca12236e47024483bdc4347a94dfdec8
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188083B2

반응 노트

불러오는 중…