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

HRID 2039492노트

반응식

HRID 2039492 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:28])[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.C(N(C(C)C)C(C)C)C>O1CCCC1>[F:21][C:22]1([F:28])[CH2:27][CH2:26][N:25]([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)[CH2:24][CH2:23]1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 27583514,4-Difluoropiperidine hydrochlorideHCID 866352552-(6-Chloropyrimidin-4-yl)-4-(1H-imidazol-1-yl)-1,2-dihydro-3H-pyrazol-3-one hydrochloride

생성물 1

HCID 444648642-[6-(4,4-Difluoropiperidin-1-yl)pyrimidin-4-yl]-4-(1H-imidazol-1-yl)-1,2-dihydro-3H-pyrazol-3-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

100 mg (0.3 mmol) of the compound from Example 13A, 63 mg (0.4 mmol) of 4,4-difluoropiperidine hydrochloride and 116 μl (86 mg, 0.7 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 2.5 h. After concentration under reduced pressure, the residue is taken up in acetonitrile/water and purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient). Yield: 82 mg (71% of theory)

후처리

  1. customreacted in a single mode microwave (Emrys Optimizer) at 120° C. for 2.5 h
  2. concentrationAfter concentration under reduced pressure
  3. custompurified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient)

출처 및 근거

ORD 기록
ord-e2b4027a1e20414682e1eee59bdd761e
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580778B2

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