1,4-Dioxane → HCID 57377354, compound

HRID 72555Notes

Reaction equation

HRID 72555 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:24]2[CH2:28][CH2:27][CH:26]([O:29][C:30]3[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=3)[CH2:25]2)=[C:6]([CH:23]=1)[C:7]([NH:9][C:10]1([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=[O:18])=[CH:15][CH:14]=2)[CH2:12][CH2:11]1)=[O:8].O1CCOCC1.O.[OH-].[Li+]>O>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:24]2[CH2:28][CH2:27][CH:26]([O:29][C:30]3[CH:31]=[CH:32][C:33]([C:36]([F:37])([F:39])[F:38])=[CH:34][CH:35]=3)[CH2:25]2)=[C:6]([CH:23]=1)[C:7]([NH:9][C:10]1([C:13]2[CH:14]=[CH:15][C:16]([C:17]([OH:19])=[O:18])=[CH:21][CH:22]=2)[CH2:12][CH2:11]1)=[O:8]

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 168937Lithium hydroxide, monohydrateHCID 67958319HCID 67958319, compound

Product 1

HCID 57377354HCID 57377354, compoundYield 6.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of methyl 4-(1-(5-chloro-2-(3-(4-(trifluoromethyl)phenoxy)pyrrolidin-1-yl)nicotinamido)cyclopropyl)benzoate (D199) (24 mg, 0.428 mmol) in a mixture 1,4-dioxane and water (3 ml/1 ml) lithium hydroxide monohydrate (2.7 mg, 0.064 mmol) was added and the mixture was stirred 2 days at room temperature. After solvent evaporation the residue was diluted with water (5 ml) and HCl 1M (15 ml) and extracted with ethylacetate (3×20 ml). Collected organics after solvent evaporation gave the title compound (E73) (15 mg) as racemic mixture.

Workup

  1. customAfter solvent evaporation the residue
  2. additionwas diluted with water (5 ml) and HCl 1M (15 ml)
  3. extractionextracted with ethylacetate (3×20 ml)
  4. customCollected organics after solvent evaporation

Sources & evidence

ORD record
ord-685b89d02421444e83c25d3dc76f75e9
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Reaction notes

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