Sodium Hydroxide → 4-(4-(1-(5-amino-2',4'-difluorobiphenyl-3-yl)-1H-benzo[d]imidazol-5-yl)-1H-1,2,3-triazol-1-yl)-2-methylbutan-2-ol

HRID 64098Notes

Reaction equation

HRID 64098 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[C:13]([N:15]2[C:19]3[CH:20]=[CH:21][C:22]([C:24]4[N:25]=[N:26][N:27]([CH2:29][CH2:30][C:31]([OH:34])([CH3:33])[CH3:32])[CH:28]=4)=[CH:23][C:18]=3[N:17]=[CH:16]2)[CH:12]=[C:11]([NH:35]C(=O)C)[CH:10]=1.[OH-].[Na+]>C(O)C>[NH2:35][C:11]1[CH:12]=[C:13]([N:15]2[C:19]3[CH:20]=[CH:21][C:22]([C:24]4[N:25]=[N:26][N:27]([CH2:29][CH2:30][C:31]([CH3:33])([OH:34])[CH3:32])[CH:28]=4)=[CH:23][C:18]=3[N:17]=[CH:16]2)[CH:14]=[C:9]([C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])[CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 89501332N-(2',4'-difluoro-5-(5-(1-(3-hydroxy-3-methylbutyl)-1H-1,2,3-triazol-4-yl)-1H-benzo[d]imidazol-1-yl)biphenyl-3-yl)acetamide

Product 1

HCID 1177779384-(4-(1-(5-amino-2',4'-difluorobiphenyl-3-yl)-1H-benzo[d]imidazol-5-yl)-1H-1,2,3-triazol-1-yl)-2-methylbutan-2-olYield 38%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of the compound of Example 44 (400 mg, 0.77 mmol) in ethanol (20 ml) was added aqueous solution of NaOH (385 mg, 9.63 mmol, 12.5 eq.) and the mixture was heated at 90° C. for 3 h. The mixture was quenched and extracted as in Example 1(d). The solvent was distilled off to give the product in 38% yield (140 mg).

Workup

  1. customThe mixture was quenched
  2. extractionextracted as in Example 1(d)
  3. distillationThe solvent was distilled off
  4. customto give the product in 38% yield (140 mg)

Sources & evidence

ORD record
ord-8243a5016ee2402c8fa11bd45173a00b
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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