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

HRID 2039503Notes

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: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:35]=[C:36]([N:42]1[CH:46]=[C:45]([C:47]#[N:48])[N:44]=[N:43]1)[C:37](OCC)=[O:38]>O>[F:11][C:12]1([F:16])[CH2:15][N:14]([C:2]2[N:3]=[CH:4][N:5]=[C:6]([N:8]3[C:37](=[O:38])[C:36]([N:42]4[CH:46]=[C:45]([C:47]#[N:48])[N:44]=[N:43]4)=[CH:35][NH:9]3)[CH:7]=2)[CH2:13]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 120 mg (0.8 mmol) of the compound from Example 11A, 129 mg (1.0 mmol) of 3,3-difluoroazetidine hydrochloride and 174 ml (129 mg, 1.0 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 32 μl (47 mg, 0.4 mmol) of trifluoroacetic acid and 194 mg (0.8 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: 51 mg (18% 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-9e554c2dbaf745978767282b1004c08a
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580778B2

Reaction notes

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