Picolinic acid → N-(3-methyl-4-oxo-2-(3-(trifluoromethyl)phenyl)-3,4-dihydroquinazolin-8-yl)picolinamide

HRID 520439

Reaction equation

[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=1)[N:8]([CH3:22])[C:7]2=[O:23].[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30](O)=[O:31].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOCC.O>[CH3:22][N:8]1[C:7](=[O:23])[C:6]2[C:11](=[C:2]([NH:1][C:30](=[O:31])[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][N:24]=3)[CH:3]=[CH:4][CH:5]=2)[N:10]=[C:9]1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=1

Participants

Conditions

Temperature: 55 °C

Procedure

A mixture of 8-amino-3-methyl-2-(3-(trifluoromethyl)phenyl)quinazolin-4(3H)-one 5 (106 mg, 0.33 mmol), pyridine-2-carboxylic acid 6 (84 mg, 0.68 mmol), HATU (263 mg, 0.69 mmo) and DIPEA (208 mg) in DMF were heated at 55° C. for 2.5 h then poured into H2O. The resulting precipitate was collected by filtration, rinsed with H2O, then Et2O to give Compound 239 as a yellow solid (130 mg, 93% yield). MS (ESI) calc. for C22H15F3N4O2: 424.11. found: 425 [M+H].

Workup

filtrationThe resulting precipitate was collected by filtration
washrinsed with H2O

Sources & evidence

ORD record: ord-50d484079dd847f5b3902c0eeb4e7211
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09326986B2

Linked notes

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