Hydrochloric Acid → HCID 67288840, compound

HRID 1626421Notes

Reaction equation

HRID 1626421 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:36])[NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]4[CH:33]=[CH:32][C:31]([CH3:34])=[C:30]([CH3:35])[CH:29]=4)[N:23]=3)=[CH:16][CH:15]=1)[O:9][CH2:8][CH2:7][CH:6]2[C:37]([O:39]C)=[O:38])#[N:2].O.[OH-].[Li+].O.Cl.O1CCOCC1>C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:36])[NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]4[CH:33]=[CH:32][C:31]([CH3:34])=[C:30]([CH3:35])[CH:29]=4)[N:23]=3)=[CH:16][CH:15]=1)[O:9][CH2:8][CH2:7][CH:6]2[C:37]([OH:39])=[O:38])#[N:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 312751,4-DioxaneHCID 168937Lithium hydroxide, monohydrateHCID 67287030HCID 67287030, compound

Product 1

HCID 67288840HCID 67288840, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 6-cyano-7-(4-(6-(3,4-dimethylphenyl)pyridin-2-ylcarbamoyl)phenoxy)-chroman-4-carboxylate (51.1 mg, 0.09577 mmol), 1.0 M lithium hydroxide monohydrate solution in water (191.5 μl, 0.1915 mmol), and THF (1.5 ml) was stirred for 3 days at ambient temperature. The mixture was quenched with 4.0 M HCl solution in 1,4-dioxane (71.83 μl, 0.2873 mmol). The mixture was purified on silica gel (MeOH in dichloromethane gradient with 1% acetic acid) to provide 42.8 mg of the title compound was obtained as a thin film (86%). MS (apci) m/z=520.2 (M+H).

Workup

  1. customThe mixture was purified on silica gel (MeOH in dichloromethane gradient with 1% acetic acid)

Sources & evidence

ORD record
ord-8cfea8aa99024a529ef2239dce121ef2
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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