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

HRID 64093
Notes
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Reaction equation

HRID 64093 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71554148N-(2',4'-difluoro-5-(5-(oxazol-5-yl)-1H-benzo[d]imidazol-1-yl)biphenyl-3-yl)acetamide

Product 1

HCID 1177780362',4'-difluoro-5-(5-(oxazol-5-yl)-1H-benzo[d]imidazol-1-yl)biphenyl-3-amineYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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

  1. customThe mixture was quenched
  2. extractionextracted as in Example 1(d)
  3. distillationThe solvent was distilled off
  4. customto afford the product in 69% yield (0.5 g)
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes