Sodium Hydroxide → HCID 178491276, compound

HRID 518678Notes

Reaction equation

HRID 518678 reaction equation
[F:1][C:2]1[CH:50]=[CH:49][C:5]([C:6]([N:8](C(=O)C2C=CC(F)=CC=2)[C:9]2[N:13]([C@H:14]3[CH2:19][CH2:18][C@@H:17]([C:20](=[O:25])[NH:21][CH:22]([CH3:24])[CH3:23])[CH2:16][CH2:15]3)[C:12]3[CH:26]=[C:27]([O:30][CH2:31][C:32]4[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=4)[CH:28]=[CH:29][C:11]=3[N:10]=2)=[O:7])=[CH:4][CH:3]=1.O1CCOCC1.[OH-].[Na+]>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][C:9]2[N:13]([C@H:14]3[CH2:19][CH2:18][C@@H:17]([C:20](=[O:25])[NH:21][CH:22]([CH3:24])[CH3:23])[CH2:16][CH2:15]3)[C:12]3[CH:26]=[C:27]([O:30][CH2:31][C:32]4[CH:33]=[CH:34][C:35]([O:38][CH3:39])=[CH:36][CH:37]=4)[CH:28]=[CH:29][C:11]=3[N:10]=2)=[O:7])=[CH:49][CH:50]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 178491275HCID 178491275, compound

Product 1

HCID 178491276HCID 178491276, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-fluoro-N-(4-fluorobenzoyl)-N-(1-(cis-4-(isopropylcarbamoyl)cyclohexyl)-6-(4-methoxybenzyloxy)-1H-benzo[d]imidazol-2-yl)benzamide (442 mg, 0.649 mmol, as a mixture with the mono-acylated material) in MeOH (3.2 mL) and dioxane (3.2 mL) was added a flake of sodium hydroxide (46.7 mg, 1.169 mmol), and the mixture was stirred at RT for 1 hour. The mixture was evaporated and the residue diluted with DCM, washed with 1 N aqueous NaOH, brine, and the organic layer dried over Na2SO4. The residue was purified via flash chromatography using a linear gradient of 0% to 50% EtOAc in hexanes. The title compound was collected as a white solid (275 mg, 76% yield). M/Z calc'd for C32H35FN4O4: 558.65. found 559 [M+H].

Workup

  1. customThe mixture was evaporated
  2. additionthe residue diluted with DCM
  3. washwashed with 1 N aqueous NaOH, brine
  4. dry with materialthe organic layer dried over Na2SO4
  5. customThe residue was purified via flash chromatography

Sources & evidence

ORD record
ord-ffd2f2367bd9428182d19c6c3aa052ae
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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