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

HRID 562471Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([NH:8][NH2:9])[N:5]=[CH:4][N:3]=1.Cl.[F:11][C:12]1([F:18])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(N(C(C)C)C(C)C)C.FC(F)(F)C(O)=O.CN([CH:38]=[C:39]([N:45]1[CH:49]=[C:48]([C:50]#[N:51])[N:47]=[CH:46]1)[C:40](OCC)=[O:41])C>O>[F:11][C:12]1([F:18])[CH2:17][CH2:16][N:15]([C:2]2[N:3]=[CH:4][N:5]=[C:6]([N:8]3[C:40](=[O:41])[C:39]([N:45]4[CH:49]=[C:48]([C:50]#[N:51])[N:47]=[CH:46]4)=[CH:38][NH:9]3)[CH:7]=2)[CH2:14][CH2:13]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 200 mg (1.4 mmol) of the compound from Example 11A, 262 mg (1.7 mmol) of 4,4-difluoropiperidine hydrochloride 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 16 h. Following the addition of 53 μl (79 mg, 0.7 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: 111 mg (21% 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-9c75be9308c2421fb27dfb74cb20cc88
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067407B2

Reaction notes

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