Sodium Hydroxide → HCID 117777395, compound

HRID 64115Notes

Reaction equation

HRID 64115 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)[N: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:26]=[CH:25][CH:24]=[CH:23]5)[CH:21]=4)[NH2:27])[CH:14]=[N:15][C:11]=3[CH:10]=2)[N:6]=[N:5]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 89501302N-(3-(5-(1-methyl-1H-1,2,3-triazol-4-yl)-1H-benzo[d]imidazol-1-yl)-5-(1H-pyrrol-1-yl)phenyl)acetamide

Product 1

HCID 117777395HCID 117777395, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 20% sodium hydroxide (5 ml) and the compound of Example 99 (1.0 g, 2.52 mmol) in 10 ml ethanol was heated at 100° C. for 3 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 residue was purified by column chromatography over silica gel to afford the product in 73% yield (0.65 g). LC-MS (ESI): Calculated mass: 355.4; Observed mass: 356.3 [M+H]+ (rt: 0.49 min).

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 residue was purified by column chromatography over silica gel
  4. customto afford the product in 73% yield (0.65 g)
  5. custom356.3 [M+H]+ (rt: 0.49 min)

Sources & evidence

ORD record
ord-50efbbc493fe4d9dbd50d1fb42c0fc74
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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