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

HRID 2039499Notes

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:17])[CH2:16][CH2:15][NH:14][CH2:13]1.C(N(C(C)C)C(C)C)C.FC(F)(F)C(O)=O.CN(C)[CH:36]=[C:37]([N:43]1[CH:47]=[C:46]([C:48]#[N:49])[N:45]=[N:44]1)[C:38](OCC)=[O:39]>O>[F:11][C:12]1([F:17])[CH2:16][CH2:15][N:14]([C:2]2[N:3]=[CH:4][N:5]=[C:6]([N:8]3[C:38](=[O:39])[C:37]([N:43]4[CH:47]=[C:46]([C:48]#[N:49])[N:45]=[N:44]4)=[CH:36][NH:9]3)[CH:7]=2)[CH2:13]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 200 mg (1.4 mmol) of the compound from Example 11A, 238 mg (1.7 mmol) of 3,3-difluoropyrrolidine 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 325 mg (1.4 mmol) of the compound from Example 7A, 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: 137 mg (27% 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-35473aa18f8b40dc98ffe74910fd584a
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580778B2

Reaction notes

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