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

HRID 415896Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

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

Workup

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

Sources & evidence

ORD record: ord-13cdc0114f3e46f49c120b595d18dbd6
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088794B2

Reaction notes

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