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Diisopropylethylamine → 2-[6-(3,3-Difluoroazetidin-1-yl)pyrimidin-4-yl]-4-(1H-imidazol-1-yl)-1,2-dihydro-3H-pyrazol-3-one

HRID 562477
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HRID 562477 반응식
Cl.Cl[C:3]1[N:8]=[CH:7][N:6]=[C:5]([N:9]2[C:13](=[O:14])[C:12]([N:15]3[CH:19]=[CH:18][N:17]=[CH:16]3)=[CH:11][NH:10]2)[CH:4]=1.Cl.[F:21][C:22]1([F:26])[CH2:25][NH:24][CH2:23]1.C(N(C(C)C)C(C)C)C>O1CCCC1>[F:21][C:22]1([F:26])[CH2:25][N:24]([C:3]2[N:8]=[CH:7][N:6]=[C:5]([N:9]3[C:13](=[O:14])[C:12]([N:15]4[CH:19]=[CH:18][N:17]=[CH:16]4)=[CH:11][NH:10]3)[CH:4]=2)[CH2:23]1
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참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 27582473,3-Difluoroazetidine hydrochlorideHCID 866352552-(6-Chloropyrimidin-4-yl)-4-(1H-imidazol-1-yl)-1,2-dihydro-3H-pyrazol-3-one hydrochloride

생성물 1

HCID 444651272-[6-(3,3-Difluoroazetidin-1-yl)pyrimidin-4-yl]-4-(1H-imidazol-1-yl)-1,2-dihydro-3H-pyrazol-3-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran
용매

실험 절차

100 mg (0.3 mmol) of the compound from Example 13A, 52 mg (0.4 mmol) of 3,3-difluoroazetidine hydrochloride and 175 μl (130 mg, 1.0 mmol) of N-ethyl-N-(propan-2-yl)propane-2-amine are initially charged in 2 ml of tetrahydrofuran and reacted in a single mode microwave (Emrys Optimizer) at 120° C. for 3 h. The precipitated solid is filtered off and the filtrate is concentrated under reduced pressure. The residue is taken up in acetonitrile/water and purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient). Yield: 36 mg (32% of theory)

후처리

  1. customreacted in a single mode microwave (Emrys Optimizer) at 120° C. for 3 h
  2. filtrationThe precipitated solid is filtered off
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. custompurified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient)

출처 및 근거

ORD 기록
ord-dc2a75ed8cb14021815e7154a722e23b
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08067407B2

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