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

HRID 64100Notes

Reaction equation

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

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of the compound of Example 53 (0.6 g, 1.41 mmol) in ethanol (20 ml) was added aqueous solution of NaOH (451 mg, 11.3 mmol, 8.0 eq.) and the mixture was heated at 85° C. for 4 h. The mixture was quenched and extracted as in Example 1(d). The solvent was distilled off to afford the product in 44% yield (0.24 g). LC-MS (ESI): Calculated mass: 383.42; Observed mass: 384.1 [M+H]+ (rt: 1.004 min).

Workup

customThe mixture was quenched
extractionextracted as in Example 1(d)
distillationThe solvent was distilled off
customto afford the product in 44% yield (0.24 g)
custom384.1 [M+H]+ (rt: 1.004 min)

Sources & evidence

ORD record: ord-c046077a47f74eee9719828dc0a7bbe1
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447091B2

Reaction notes

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