Sodium Hydroxide → HCID 117777819, compound

HRID 64111Notes

Reaction equation

HRID 64111 reaction equation
[OH-].[Na+].[CH3:3][N:4]1[CH:8]=[C:7]([C:9]2[CH:32]=[CH:31][C:12]3[N:13]([C:16]4[CH:17]=[C:18]([NH:27]C(=O)C)[CH:19]=[C:20]([N:22]5[CH:26]=[CH:25][CH:24]=[CH:23]5)[CH:21]=4)[CH:14]=[N:15][C:11]=3[CH:10]=2)[CH:6]=[N:5]1>C(O)C.C(OCC)(=O)C>[CH3:3][N:4]1[CH:8]=[C:7]([C:9]2[CH:32]=[CH:31][C:12]3[N:13]([C:16]4[CH:17]=[C:18]([CH:19]=[C:20]([N:22]5[CH:23]=[CH:24][CH:25]=[CH:26]5)[CH:21]=4)[NH2:27])[CH:14]=[N:15][C:11]=3[CH:10]=2)[CH:6]=[N:5]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 117777504HCID 117777504, compound

Product 1

HCID 117777819HCID 117777819, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 20% sodium hydroxide (5 ml) and the compound of Example 87 (1.15 g, 2.9 mmol) in 25 ml ethanol was heated at 100° C. for 2 h. The mixture was diluted with ethyl acetate (100 ml) and the organic layer was washed with water (50 ml) and brine (25 ml). The solvent was removed under reduced pressure and the crude was purified by column chromatography over silica gel to give the product in 68% yield (0.7 g).

Workup

  1. washthe organic layer was washed with water (50 ml) and brine (25 ml)
  2. customThe solvent was removed under reduced pressure
  3. customthe crude was purified by column chromatography over silica gel
  4. customto give the product in 68% yield (0.7 g)

Sources & evidence

ORD record
ord-6ef5c327d86a4ef19e6b8e1eeaee8ca4
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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