Triethylamine → N-(7-chloro-2,3-dihydro-1H-inden-1-yl)-N-cyclopropyl-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide

HRID 2194986노트

반응식

HRID 2194986 반응식
[F:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=1[C:9](Cl)=[O:10].[Cl:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:21]=1[CH:20]([NH:22][CH:23]1[CH2:25][CH2:24]1)[CH2:19][CH2:18]2.C(N(CC)CC)C.CCCCCCC.C(OCC)(=O)C>O1CCCC1>[Cl:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:21]=1[CH:20]([N:22]([CH:23]1[CH2:25][CH2:24]1)[C:9]([C:3]1[C:4]([CH3:8])=[N:5][N:6]([CH3:7])[C:2]=1[F:1])=[O:10])[CH2:19][CH2:18]2

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 108668795-Fluoro-1,3-dimethyl-1H-pyrazole-4-carbonyl chlorideHCID 21899848Ethylacetate heptaneHCID 684283077-chloro-N-cyclopropyl-2,3-dihydro-1H-inden-1-amine

생성물 1

HCID 68429771N-(7-chloro-2,3-dihydro-1H-inden-1-yl)-N-cyclopropyl-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide수율 73%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

At ambient temperature, a solution of 0.19 g (1.06 mmol) of 5-fluoro-1,3-dimethyl-1H-pyrazole-4-carbonyl chloride in 3 ml of tetrahydrofurane is added dropwise to a solution of 0.20 g (0.96 mmol) of 7-chloro-N-cyclopropyl-2,3-dihydro-1H-inden-1-amine and 0.15 ml triethylamine in 8 ml tetrahydrofurane. The reaction mixture is stirred for 3 hrs at reflux. The solvent is removed under vacuum and 10 ml of water are then added to the residue. The watery layer is extracted three times with ethyl acetate (3×20 ml); the combined organic layers are dried over magnesium sulphate and concentrated in vacuum. Column chromatography (gradient n-heptane/ethyl acetate) yields 0.26 mg (73% yield) of N-(7-chloro-2,3-dihydro-1H-inden-1-yl)-N-cyclopropyl-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide as an orange oil (M+1=348).

후처리

  1. temperatureat reflux
  2. customThe solvent is removed under vacuum and 10 ml of water
  3. additionare then added to the residue
  4. extractionThe watery layer is extracted three times with ethyl acetate (3×20 ml)
  5. dry with materialthe combined organic layers are dried over magnesium sulphate
  6. concentrationconcentrated in vacuum

출처 및 근거

ORD 기록
ord-2ae1423e97d042449efc25bcf4299670
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08334390B2

반응 노트

불러오는 중…