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

HRID 64089Notes

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[CH: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[CH: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 N-(2′,4′-difluoro-5-(5-(1-methyl-1H-pyrazol-4-yl)-1H-benzo-[d]imidazol-1-yl)biphenyl-3-yl)acetamide of Example 1 (1.0 g, 2.26 mmol) in ethanol (10 ml) was added aqueous solution of NaOH (800 mg, 20 mmol, 8.9 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 under reduced pressure to afford the product in 66% yield (0.6 g). LC-MS (ESI): Calculated mass: 401.41; Observed mass: 402.1 [M+H]+ (rt: 1.198 min).

Workup

customThe mixture was quenched
extractionextracted as in Example 1(d)
distillationThe solvent was distilled off under reduced pressure
customto afford the product in 66% yield (0.6 g)
custom402.1 [M+H]+ (rt: 1.198 min)

Sources & evidence

ORD record: ord-0533b67047f74c30bcc10e247ef728d6
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447091B2

Reaction notes

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