Sodium Hydroxide → 3-(5-(1H-pyrazol-1-yl)-1H-benzo[d]imidazol-1-yl)-5-(1H-pyrazol-1-yl)aniline

HRID 64123Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of the compound of Example 122 (230 mg, 0.6 mmol) in ethanol (20 ml) was added aqueous solution of sodium hydroxide (192 mg, 4.8 mmol, 8.0 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 afford the product in 73% yield (150 mg).

Workup

customThe mixture was quenched
extractionextracted as in Example 1(d)
distillationThe solvent was distilled off
customto afford the product in 73% yield (150 mg)

Sources & evidence

ORD record: ord-a5d42b0336614331b560a66a014dfa40
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447091B2

Reaction notes

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