Potassium Hydroxide → HCID 89501197, compound

HRID 64179Notes

Reaction equation

HRID 64179 reaction equation
[C:1]([C:3]1[CH:29]=[CH:28][C:6]2[N:7]([C:10]3[CH:11]=[C:12]([NH:24]C(=O)C)[CH:13]=[C:14]([C:16]4[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=4[F:23])[CH:15]=3)[CH:8]=[N:9][C:5]=2[CH:4]=1)#[N:2].[OH-:30].[K+]>C(O)C>[NH2:24][C:12]1[CH:11]=[C:10]([N:7]2[C:6]3[CH:28]=[CH:29][C:3]([C:1]([NH2:2])=[O:30])=[CH:4][C:5]=3[N:9]=[CH:8]2)[CH:15]=[C:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[F:23])[CH:13]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 89501166HCID 89501166, compound

Product 1

HCID 89501197HCID 89501197, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of N-(5-(5-cyano-1H-benzo[d]imidazol-1-yl)-2′,4′-difluoro-[1,1′-biphenyl]-3-yl)acetamide (0.5 g, 1.28 mmol, 1 eq.) in ethanol (10 ml) was added 20% aqueous solution of potassium hydroxide (0.721 g, 12.88 mmol, 10 eq.) and the mixture was heated at 85° C. for 5 h. The mixture was quenched and extracted as in Example 1(d). The solvent was distilled off to afford title product in 71% yield (0.32 g). LC-MS (ESI): Calculated mass: 364.11; Observed mass: 365.1 [M+H]+ (rt: 0.59 min).

Workup

  1. customThe mixture was quenched
  2. extractionextracted as in Example 1(d)
  3. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-e995a82486ca479db601818bbdddc308
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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