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

HRID 562483Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([NH:8][NH2:9])[N:5]=[CH:4][N:3]=1.Cl.[O:11]1[CH2:16][CH2:15][CH2:14][CH2:13][NH:12]1.C(N(C(C)C)C(C)C)C.FC(F)(F)C(O)=O.CN([CH:36]=[C:37]([N:43]1[CH:47]=[C:46]([C:48]#[N:49])[N:45]=[CH:44]1)[C:38](OCC)=[O:39])C>O>[O:11]1[CH2:16][CH2:15][CH2:14][CH2:13][N:12]1[C:2]1[N:3]=[CH:4][N:5]=[C:6]([N:8]2[C:38](=[O:39])[C:37]([N:43]3[CH:47]=[C:46]([C:48]#[N:49])[N:45]=[CH:44]3)=[CH:36][NH:9]2)[CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 200 mg (1.4 mmol) of the compound from Example 11A, 205 mg (1.7 mmol) of 1,2-oxazinane hydrochloride [Bhat et al., J. Chem. Soc. Perkin Trans. 2 2000, 7, 1435-1446] and 289 μl (215 mg, 1.7 mmol) of N-ethyl-N-(propan-2-yl)propane-2-amine in 3 ml of water is stirred at 100° C. for 1.5 h. Following the addition of 59 μl (49 mg, 0.4 mmol) of trifluoroacetic acid and 324 mg (1.4 mmol) of the compound from Example 6A, 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: 199 mg (39% of theory)

Workup

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

Sources & evidence

ORD record: ord-8c45433329ec404484d6a3c65b869fd6
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067407B2

Reaction notes

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