Sodium Hydroxide → 5-(5-(1-(2-(dimethylamino)ethyl)-1H-1,2,3-triazol-4-yl)-1H-benzo[d]-imidazol-1-yl)-2',4'-difluorobiphenyl-3-amine

HRID 64096

Reaction equation

HRID 64096 reaction equation
[CH3:1][N:2]([CH3:37])[CH2:3][CH2:4][N:5]1[CH:9]=[C:8]([C:10]2[CH:36]=[CH:35][C:13]3[N:14]([C:17]4[CH:18]=[C:19]([NH:31]C(=O)C)[CH:20]=[C:21]([C:23]5[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=5[F:30])[CH:22]=4)[CH:15]=[N:16][C:12]=3[CH:11]=2)[N:7]=[N:6]1.[OH-].[Na+]>C(O)C>[CH3:1][N:2]([CH3:37])[CH2:3][CH2:4][N:5]1[CH:9]=[C:8]([C:10]2[CH:36]=[CH:35][C:13]3[N:14]([C:17]4[CH:18]=[C:19]([NH2:31])[CH:20]=[C:21]([C:23]5[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=5[F:30])[CH:22]=4)[CH:15]=[N:16][C:12]=3[CH:11]=2)[N:7]=[N:6]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71554232N-(5-(5-(1-(2-(dimethylamino)ethyl)-1H-1,2,3-triazol-4-yl)-1H-benzo[d]-imidazol-1-yl)-2',4'-difluorobiphenyl-3-yl)acetamide

Product 1

HCID 1177776625-(5-(1-(2-(dimethylamino)ethyl)-1H-1,2,3-triazol-4-yl)-1H-benzo[d]-imidazol-1-yl)-2',4'-difluorobiphenyl-3-amineYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of the compound of Example 20 (450 mg, 0.9 mmol) in ethanol (10 ml) was added aqueous solution of NaOH (450 mg, 11.25 mmol, 12.5 eq.) and the mixture was heated at 85° 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 77% yield (0.32 g).

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 77% yield (0.32 g)

Sources & evidence

ORD record
ord-c3086a9091d54629acca513578b8af88
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Linked notes

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