HCID 86621901, compound → HCID 69225384, compound

HRID 1027897Notes

Reaction equation

HRID 1027897 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([N:18]2[CH2:26][CH:25]3[CH:20]([N:21]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22][CH2:23][CH2:24]3)[CH2:19]2)[C:5]2[CH2:12][CH2:11][O:10][C:9]3[CH:13]=[C:14](I)[CH:15]=[CH:16][C:8]=3[C:6]=2[N:7]=1.[Cu][C:35]#[N:36]>CN(C=O)C.CCOCC>[NH2:1][C:2]1[N:3]=[C:4]([N:18]2[CH2:26][CH:25]3[CH:20]([N:21]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22][CH2:23][CH2:24]3)[CH2:19]2)[C:5]2[CH2:12][CH2:11][O:10][C:9]3[CH:13]=[C:14]([C:35]#[N:36])[CH:15]=[CH:16][C:8]=3[C:6]=2[N:7]=1

Participants

5

Reactant 2

HCID 86621901HCID 86621901, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 69225384HCID 69225384, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

The product from Example 102A (24.7 mg, 0.044 mmol) was treated with copper(I) cyanide (27.5 mg, 0.307 mmol) in DMF (0.5 mL) heated at 110° C. overnight, cooled, diluted with Et2O (25 mL), washed with water (2×20 mL), washed with brine, dried (MgSO4), filtered, concentrated and purified by chromatography on silica gel eluting with hexane:EtOAc (2:1, 1:1, 4:1) to provide the title compound. MS (M+H)+ m/z 463.

Workup

  1. temperaturecooled
  2. washwashed with water (2×20 mL)
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by chromatography on silica gel eluting with hexane:EtOAc (2:1, 1:1, 4:1)

Sources & evidence

ORD record
ord-f6bdebd5e5e941c397c9f2087b46e953
Source dataset
uspto-grants-2014_05
Patent number
US08735411B2

Reaction notes

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