Methanol → HCID 67288340, compound

HRID 1626394Notes

Reaction equation

HRID 1626394 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]1[N:8]=[CH:7][C:6]([NH:9][C:10]([C:12]2[CH:34]=[CH:33][C:15]([O:16][C:17]3[CH:26]=[C:25]4[C:20]([CH:21]([C:27]([O:29]C)=[O:28])[CH2:22][CH2:23][O:24]4)=[CH:19][C:18]=3[C:31]#[N:32])=[CH:14][CH:13]=2)=[O:11])=[CH:5][CH:4]=1.[OH-].[Na+].CO>C1COCC1.C(OCC)(=O)C.Cl>[F:36][C:2]([F:1])([F:35])[C:3]1[N:8]=[CH:7][C:6]([NH:9][C:10]([C:12]2[CH:13]=[CH:14][C:15]([O:16][C:17]3[CH:26]=[C:25]4[C:20]([CH:21]([C:27]([OH:29])=[O:28])[CH2:22][CH2:23][O:24]4)=[CH:19][C:18]=3[C:31]#[N:32])=[CH:33][CH:34]=2)=[O:11])=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 67287730HCID 67287730, compound

Product 1

HCID 67288340HCID 67288340, compoundYield 21.9%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 7-(4-((6-(trifluoromethyl)pyridin-3-yl)carbamoyl)phenoxy)-6-cyanochroman-4-carboxylate (141 mg, 0.283 mmol) was diluted with THF (1 mL) followed by the addition of sodium hydroxide (0.31 mL, 0.31 mmol) and methanol (300 μL). After stirring for 2 hours, the reaction was diluted with ethyl acetate and 1N HCl. The layers were separated and the organic layer was dried over magnesium sulfate, filtered and concentrated. The material was diluted with dichloromethane and a white precipitate formed which was filtered and rinsed with dichloromethane to provide the desired product (30 mg, 21.9% yield). MS (ESI)=484.1 (M+1).

Workup

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. additionThe material was diluted with dichloromethane
  6. customa white precipitate formed which
  7. filtrationwas filtered
  8. washrinsed with dichloromethane

Sources & evidence

ORD record
ord-eff6ae55d7a247aeb35fb245b03e7d16
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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