HCID 86725349, compound → HCID 86725351, compound

HRID 925242Notes

Reaction equation

HRID 925242 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]([N:5]1[CH2:24][CH2:23][C:9]2[C:10]3[C:11](O)([C:17]4[S:18][CH:19]=[CH:20][N:21]=4)[CH2:12][CH2:13][C:14]=3[CH:15]=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4]>Cl.O1CCOCC1>[F:26][C:2]([F:1])([F:25])[C:3]([N:5]1[CH2:24][CH2:23][C:9]2[C:10]3[C:11]([C:17]4[S:18][CH:19]=[CH:20][N:21]=4)=[CH:12][CH2:13][C:14]=3[CH:15]=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4]

Participants

3

Reactant 1

HCID 86725349HCID 86725349, compound

Product 1

HCID 86725351HCID 86725351, compoundYield 5.3%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Conditions

Temperature
60 °C

Procedure

The product from step (b) (1.13 mmol) was dissolved in 4N HCl/dioxane and heated to 60° C. for 1 hour after which time LCMS indicated no starting material. The reaction mixture was cooled to RT and the solvent was evaporated in vacuo to give the crude product as a brown semi-solid. Purification by flash silica-gel chromatography (gradient elution: 0-50% EtOAc in hexanes) gave the sub-title compound (22 mg) as a yellow oil. MS: ESI (positive): 365 (M+H).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. customthe solvent was evaporated in vacuo
  3. customto give the crude product as a brown semi-solid
  4. customPurification
  5. washby flash silica-gel chromatography (gradient elution: 0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-cdf2d04feca847fabb5a096516478b79
Source dataset
uspto-grants-2016_03
Patent number
US09284277B2

Reaction notes

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