Sodium Hydroxide → 2',4'-difluoro-5-(5-(1-methyl-1H-1,2,3-triazol-4-yl)-1H-benzo[d]imidazol-1-yl)biphenyl-3-amine

HRID 64092Notes

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]([CH3:29])[CH:28]=4)=[CH:23][C:18]=3[N:17]=[CH:16]2)[CH:12]=[C:11]([NH:30]C(=O)C)[CH:10]=1.[OH-].[Na+]>C(O)C>[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]([CH3:29])[CH:28]=4)=[CH:23][C:18]=3[N:17]=[CH:16]2)[CH:12]=[C:11]([NH2:30])[CH:10]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of the compound of Example 17 (300 mg, 0.675 mmol) in ethanol (10 ml) was added aqueous solution of NaOH (338 mg, 8.44 mmol, 12.5 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 the product in 44% yield (0.12 g). LC-MS (ESI): Calculated mass: 402.4; Observed mass: 403.4 [M+H]+ (rt: 1.03 min).

Workup

customThe mixture was quenched
extractionextracted as in Example 1(d)
distillationThe solvent was distilled off
customto afford the product in 44% yield (0.12 g)
custom403.4 [M+H]+ (rt: 1.03 min)

Sources & evidence

ORD record: ord-352070ae40124942b29defc91b241676
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447091B2

Reaction notes

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