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

HRID 2039505Notes

Reaction equation

HRID 2039505 reaction equation
CN(C)[CH:3]=[C:4]([N:10]1[CH:14]=[C:13]([C:15]#[N:16])[N:12]=[N:11]1)[C:5](OCC)=[O:6].[NH:18]([C:20]1[N:25]=[CH:24][N:23]=[C:22]([N:26]2[CH2:32][CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[CH:21]=1)[NH2:19].FC(F)(F)C(O)=O>O>[O:29]1[CH2:30][CH2:31][CH2:32][N:26]([C:22]2[N:23]=[CH:24][N:25]=[C:20]([N:18]3[C:5](=[O:6])[C:4]([N:10]4[CH:14]=[C:13]([C:15]#[N:16])[N:12]=[N:11]4)=[CH:3][NH:19]3)[CH:21]=2)[CH2:27][CH2:28]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 579250704-(6-Hydrazinylpyrimidin-4-yl)-1,4-oxazepaneHCID 66725972Ethyl 2-(4-cyanotriazol-1-yl)-3-(dimethylamino)prop-2-enoate

Product 1

HCID 579250661-{2-[6-(1,4-Oxazepan-4-yl)pyrimidin-4-yl]-3-oxo-2,3-dihydro-1H-pyrazol-4-yl}-1H-1,2,3-triazole-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 200 mg (0.9 mmol) of the compound from Example 7A, 178 mg (0.9 mmol) of the compound from Example 14A and 33 ml (49 mg, 0.4 mmol) of trifluoroacetic acid in 3 ml of water 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: 80 mg (27% of theory) LC-MS (Method 4): Rt=1.40 min; MS (ESIpos): m/z=354 [M+H]+;

Workup

  1. filtrationThe precipitated solid is filtered off
  2. washwashed first with water
  3. customThe product is dried under reduced pressure

Sources & evidence

ORD record
ord-cd47685969344b759f6d28e957af118e
Source dataset
uspto-grants-2013_11
Patent number
US08580778B2

Reaction notes

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