Triethylamine hydrochloride → 6-Chloro-3-(2-fluorophenyl)-7-(thien-2-yl)-1,2,4-triazolo[4,3-b]pyridazine

HRID 2306586노트

반응식

HRID 2306586 반응식
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][C:7]=1[C:8]1[S:9][CH:10]=[CH:11][CH:12]=1.[F:14][C:15]1[CH:24]=[CH:23][CH:22]=[CH:21][C:16]=1[C:17]([NH:19][NH2:20])=O.Cl.C(N(CC)CC)C>CC1C=CC(C)=CC=1>[Cl:1][C:2]1[C:7]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)=[CH:6][C:5]2[N:4]([C:17]([C:16]3[CH:21]=[CH:22][CH:23]=[CH:24][C:15]=3[F:14])=[N:19][N:20]=2)[N:3]=1

참가 물질

5

반응물 3

HCID 11130Triethylamine hydrochlorideHCID 1362882-FluorobenzhydrazideHCID 226099503,6-Dichloro-4-(thien-2-yl)pyridazine

생성물 1

HCID 226098966-Chloro-3-(2-fluorophenyl)-7-(thien-2-yl)-1,2,4-triazolo[4,3-b]pyridazine수율 26%

시약·촉매·용매 1

HCID 7809P-Xylene용매

실험 절차

A mixture of 3,6-dichloro-4-(thien-2-yl)pyridazine from above (0.5 g, 2.1 mmol), 2-fluorobenzhydrazide (0.66 g, 4.3 mmol) and triethylamine hydrochloride (0.59 g, 4.3 mmol) in p-xylene (10 ml) was stirred and heated at reflux under nitrogen for 30 hours. Upon cooling the volatiles were removed in vacuo. The residue was partly purified by chromatography on silica gel eluting with 50%→66%→100% ethyl acetate-hexane to give the title compound as a yellow solid (0.19 g, 26%). MS (ES+) m/e 33 1 [MH]+, 333 [MH]+. This material was used without further purification.

후처리

  1. temperatureheated
  2. temperatureat reflux under nitrogen for 30 hours
  3. temperatureUpon cooling the volatiles
  4. customwere removed in vacuo
  5. customThe residue was partly purified by chromatography on silica gel eluting with 50%→66%→100% ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-05f41e9359894802aa0397efa2f33191
출처 데이터셋
uspto-grants-2004_12
특허 번호
US06828322B2

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