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

HRID 64093Notes

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[O:28][CH:27]=[N:26][CH:25]=4)=[CH:23][C:18]=3[N:17]=[CH:16]2)[CH:12]=[C:11]([NH:29]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[O:28][CH:27]=[N:26][CH:25]=4)=[CH:23][C:18]=3[N:17]=[CH:16]2)[CH:12]=[C:11]([NH2:29])[CH:10]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of the compound of Example 22 (800 mg, 1.86 mmol) in ethanol (10 ml) was added aqueous solution of NaOH (640 mg, 16 mmol, 8.6 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 69% yield (0.5 g). LC-MS (ESI): Calculated mass: 388.37; Observed mass: 389.1 [M+H]+ (rt: 1.517 min).

Workup

customThe mixture was quenched
extractionextracted as in Example 1(d)
distillationThe solvent was distilled off
customto afford the product in 69% yield (0.5 g)
custom389.1 [M+H]+ (rt: 1.517 min)

Sources & evidence

ORD record: ord-a76d381ed05a4e538bbc0519c60e677c
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447091B2

Reaction notes

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