Water → 7-(2,4-Difluorophenyl)-2-[1-(propan-2-yl)piperidin-4-yl][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one

HRID 2088684Notes

Reaction equation

C([O:3][C:4](=O)[NH:5]/[C:6](/[C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17])=[CH:7]\[C:8]#[N:9])C.[CH3:19][CH:20]([N:22]1[CH2:27][CH2:26][CH:25]([C:28]([NH:30][NH2:31])=O)[CH2:24][CH2:23]1)[CH3:21].O>CN1CCCC1=O>[F:17][C:11]1[CH:12]=[C:13]([F:16])[CH:14]=[CH:15][C:10]=1[C:6]1[NH:5][C:4](=[O:3])[N:31]2[N:30]=[C:28]([CH:25]3[CH2:26][CH2:27][N:22]([CH:20]([CH3:21])[CH3:19])[CH2:23][CH2:24]3)[N:9]=[C:8]2[CH:7]=1

Participants

Conditions

Temperature: 160 °C

Procedure

2.0 g (4.12 mmol) of ethyl[(Z)-2-cyano-1-(2,4-difluorophenyl)ethenyl]carbamate (Example 37A) and 916 mg (4.95 mmol) of 1-(propan-2-yl)piperidin-4-carbohydrazide (Example 38A) were dissolved in 24 ml of N-methylpyrrolidone, and the mixture was stirred under argon at an oil bath temperature of 160° C. in a flask with fitted calcium chloride drying tube for 6 h. The reaction mixture was cooled to RT, water (50 ml) was added and the mixture was stirred for 15 min. The mixture was extracted with ethyl acetate (three times 50 ml each) and the combined organic phases were freed from the solvent. The residue was purified by preparative HPLC (Method 11). This gave 660 mg (41% of theory) of the product.

Workup

temperatureThe reaction mixture was cooled to RT
stirringthe mixture was stirred for 15 min
extractionThe mixture was extracted with ethyl acetate (three times 50 ml each)
customThe residue was purified by preparative HPLC (Method 11)

Sources & evidence

ORD record: ord-78b797375ba54bd39db663c669f82413
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436003B2

Reaction notes

Loading…