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

HRID 64119Notes

Reaction equation

HRID 64119 reaction equation
[OH:1][C:2]([CH3:35])([CH3:34])[CH2:3][CH2:4][N:5]1[CH:9]=[C:8]([C:10]2[CH:33]=[CH:32][C:13]3[N:14]([C:17]4[CH:18]=[C:19]([NH:28]C(=O)C)[CH:20]=[C:21]([N:23]5[CH:27]=[CH:26][CH:25]=[CH:24]5)[CH:22]=4)[CH:15]=[N:16][C:12]=3[CH:11]=2)[N:7]=[N:6]1.[OH-].[Na+]>C(O)C>[NH2:28][C:19]1[CH:18]=[C:17]([N:14]2[C:13]3[CH:32]=[CH:33][C:10]([C:8]4[N:7]=[N:6][N:5]([CH2:4][CH2:3][C:2]([CH3:35])([OH:1])[CH3:34])[CH:9]=4)=[CH:11][C:12]=3[N:16]=[CH:15]2)[CH:22]=[C:21]([N:23]2[CH:27]=[CH:26][CH:25]=[CH:24]2)[CH:20]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 89501342N-(3-(5-(1-(3-hydroxy-3-methylbutyl)-1H-1,2,3-triazol-4-yl)-1H-benzo[d]-imidazol-1-yl)-5-(1H-pyrrol-1-yl)phenyl)acetamide

Product 1

HCID 1177775254-(4-(1-(3-amino-5-(1H-pyrrol-1-yl)phenyl)-1H-benzo[d]imidazol-5-yl)-1H-1,2,3-triazol-1-yl)-2-methylbutan-2-olYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of the compound of Example 112 (150 mg, 0.32 mmol) in ethanol (10 ml) was added aqueous solution of NaOH (160 mg, 4 mmol, 12.5 eq.) and the mixture was heated at 80° C. for 2 h. The mixture was quenched and extracted as in Example 1(d). The solvent was distilled off to afford the product in 58% yield (80 mg).

Workup

  1. customThe mixture was quenched
  2. extractionextracted as in Example 1(d)
  3. distillationThe solvent was distilled off
  4. customto afford the product in 58% yield (80 mg)

Sources & evidence

ORD record
ord-8be034cc45d547fd93b91d799ecf7013
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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