Hydrochloric Acid → HCID 178491793, compound
Reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[C:10]([C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=2[O:18][CH3:19])=[CH:9][C:8](=[O:20])[NH:7][C:6]1=[S:21].[N:22]1([C:31]([N:33]2[CH2:36][C:35]([F:38])([F:37])[CH2:34]2)=N)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.Cl>CN(C=O)C.O1CCOCC1>[F:37][C:35]1([F:38])[CH2:36][N:33]([C:31](=[NH:22])[NH:1][CH2:2][CH2:3][CH2:4][N:5]2[C:10]([C:11]3[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=3[O:18][CH3:19])=[CH:9][C:8](=[O:20])[NH:7][C:6]2=[S:21])[CH2:34]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
To a mixture of 1-(3-aminopropyl)-6-(5-fluoro-2-methoxyphenyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one (prepared in an analogous manner to Example 6; 50 mg, 0.14 mmol) and 1-(1H-benzotriazol-1-yl)-1-(3,3-difluoroazetidin-1-yl)methanimine (47.5 mg, 0.174 mmol) in DMF (0.46 mL) was added N,N-diisopropylethylamine (0.061 mL, 0.35 mmol) under nitrogen and heated at 60° C. under nitrogen for 1 h. The reaction mixture was cooled to room temperature, and treated with 4N HCl in dioxane (0.25 mL). The mixture was stirred at room temperature for 10 min, then concentrated in vacuo and azeotroped with heptanes (3×10 mL). The residue was dissolved in water (1 mL) and purified using medium pressure reverse-phase (C18) chromatography (100:0 to 70:30 water/acetonitrile) to give the title compound as a white solid (22 mg, 33%).
Workup
- customprepared in an analogous manner to Example 6
- temperatureThe reaction mixture was cooled to room temperature
- concentrationconcentrated in vacuo
- customazeotroped with heptanes (3×10 mL)
- dissolutionThe residue was dissolved in water (1 mL)
- custompurified
Sources & evidence
- ORD record
- ord-74ea1dc27ef04c4b9640ba733c30884e
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08841314B2
Reaction notes
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