Trifluoroacetic acid → 1-{2-[6-(3,3-Difluoroazetidin-1-yl)pyrimidin-4-yl]-3-oxo-2,3-dihydro-1H-pyrazol-4-yl}-1H-1,2,3-triazole-4-carbonitrile

HRID 562480노트

반응식

HRID 562480 반응식
Cl[C:2]1[CH:7]=[C:6]([NH:8][NH2:9])[N:5]=[CH:4][N:3]=1.Cl.[F:11][C:12]1([F:16])[CH2:15][NH:14][CH2:13]1.C(N(C(C)C)C(C)C)C.FC(F)(F)C(O)=O.CN(C)[CH:35]=[C:36]([N:42]1[CH:46]=[C:45]([C:47]#[N:48])[N:44]=[N:43]1)[C:37](OCC)=[O:38]>O>[F:11][C:12]1([F:16])[CH2:15][N:14]([C:2]2[N:3]=[CH:4][N:5]=[C:6]([N:8]3[C:37](=[O:38])[C:36]([N:42]4[CH:46]=[C:45]([C:47]#[N:48])[N:44]=[N:43]4)=[CH:35][NH:9]3)[CH:7]=2)[CH2:13]1

참가 물질

7

반응물 5

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 2472224-Chloro-6-hydrazinylpyrimidineHCID 27582473,3-Difluoroazetidine hydrochlorideHCID 66725972Ethyl 2-(4-cyanotriazol-1-yl)-3-(dimethylamino)prop-2-enoate

생성물 1

HCID 442516321-{2-[6-(3,3-Difluoroazetidin-1-yl)pyrimidin-4-yl]-3-oxo-2,3-dihydro-1H-pyrazol-4-yl}-1H-1,2,3-triazole-4-carbonitrile

시약·촉매·용매 1

HCID 962Water용매

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온도
100 °C

실험 절차

A mixture of 120 mg (0.8 mmol) of the compound from Example 11A, 129 mg (1.0 mmol) of 3,3-difluoroazetidine hydrochloride and 174 μl (129 mg, 1.0 mmol) of N-ethyl-N-(propan-2-yl)propane-2-amine in 3 ml of water is stirred at 100° C. for 16 h. Following the addition of 32 μl (47 mg, 0.4 mmol) of trifluoroacetic acid and 194 mg (0.8 mmol) of the compound from Example 7A, the reaction mixture is stirred at 100° C. for 16 h. The precipitated solid is filtered off and washed first with water and then with diethyl ether. The product is dried under reduced pressure. Yield: 51 mg (18% of theory)

후처리

  1. stirringthe reaction mixture is stirred at 100° C. for 16 h
  2. filtrationThe precipitated solid is filtered off
  3. washwashed first with water
  4. customThe product is dried under reduced pressure

출처 및 근거

ORD 기록
ord-d0178f75ad624aa89070549e62a4d9d0
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067407B2

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