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Hydrochloric Acid → HCID 178491793, compound

HRID 77562
Notes
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Reaction equation

HRID 77562 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]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 866847021-(1H-Benzotriazol-1-yl)-1-(3,3-difluoroazetidin-1-yl)methanimineHCID 866847051-(3-aminopropyl)-6-(5-fluoro-2-methoxyphenyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one

Product 1

HCID 178491793HCID 178491793, compoundYield 33%

Reagents, catalysts & solvents

2
HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

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

  1. customprepared in an analogous manner to Example 6
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationconcentrated in vacuo
  4. customazeotroped with heptanes (3×10 mL)
  5. dissolutionThe residue was dissolved in water (1 mL)
  6. custompurified

Sources & evidence

ORD record
ord-74ea1dc27ef04c4b9640ba733c30884e
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08841314B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes