Triethylamine → 1-Benzyl-N-(5-(7-methoxyquinolin-4-yloxy)pyridin-2-yl)-2-oxo-1,2-dihydropyrazolo[1,5-a]pyridine-3-carboxamide

HRID 415896노트

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HRID 415896 반응식
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:25]([N:32]1[N:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]2=[C:34]([C:41]([OH:43])=O)[C:33]1=[O:44])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[CH3:45][O:46][C:47]1[CH:56]=[C:55]2[C:50]([C:51]([O:57][C:58]3[CH:59]=[CH:60][C:61]([NH2:64])=[N:62][CH:63]=3)=[CH:52][CH:53]=[N:54]2)=[CH:49][CH:48]=1.C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O.O>[CH2:25]([N:32]1[N:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]2=[C:34]([C:41]([NH:64][C:61]2[CH:60]=[CH:59][C:58]([O:57][C:51]3[C:50]4[C:55](=[CH:56][C:47]([O:46][CH3:45])=[CH:48][CH:49]=4)[N:54]=[CH:53][CH:52]=3)=[CH:63][N:62]=2)=[O:43])[C:33]1=[O:44])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 595983945-(7-Methoxyquinolin-4-yloxy)pyridin-2-amineHCID 666194781-Benzyl-2-oxo-1,2-dihydropyrazolo[1,5-a]pyridine-3-carboxylic acid

생성물 1

HCID 119631431-Benzyl-N-(5-(7-methoxyquinolin-4-yloxy)pyridin-2-yl)-2-oxo-1,2-dihydropyrazolo[1,5-a]pyridine-3-carboxamide

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

A mixture of HATU (760 mg, 2.0 mmol), crude 1-benzyl-2-oxo-1,2-dihydropyrazolo[1,5-a]pyridine-3-carboxylic acid (268 mg, 1.0 mmol), 5-(7-methoxyquinolin-4-yloxy)pyridin-2-amine (220 mg, 1.0 mmol), and triethylamine (2000 μl, 14 mmol) in DMF (3 mL) plus CHCL3 (3 mL) was stirred at 60° C. for 4 days. Then, the mixture was diluted with EtOAc (10 mL) and H2O (5 mL). The organic layer was washed with NaOH (1 N), H2O, NaHCO3, and dried over Na2SO4. The organic residue was purified on silica and further purified by trituration with EtOAc in ether (5%), resulting a light green powder. Calc'd for C30H23N5O4: 517; MS (ESI pos. ion) m/z: 518

후처리

  1. washThe organic layer was washed with NaOH (1 N), H2O, NaHCO3
  2. dry with materialdried over Na2SO4
  3. customThe organic residue was purified on silica
  4. customfurther purified by trituration with EtOAc in ether (5%)
  5. customresulting a light green powder

출처 및 근거

ORD 기록
ord-13cdc0114f3e46f49c120b595d18dbd6
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088794B2

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