Hydrochloric Acid → HCID 67288468, compound

HRID 1626418Notes

Reaction equation

HRID 1626418 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:34])[NH:21][CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][N:25]=3)=[CH:16][CH:15]=1)[O:9][CH2:8][CH2:7][CH:6]2[C:35]([O:37]C)=[O:36])#[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:34])[NH:21][CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:31])([F:32])[F:33])=[CH:26][N:25]=3)=[CH:16][CH:15]=1)[O:9][CH2:8][CH2:7][CH:6]2[C:35]([OH:37])=[O:36])#[N:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 312751,4-DioxaneHCID 168937Lithium hydroxide, monohydrateHCID 67287501HCID 67287501, compound

Product 1

HCID 67288468HCID 67288468, compoundYield 36.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 6-cyano-7-(4-(2-(5-(trifluoromethyl)-pyridin-2-yl)ethylcarbamoyl)phenoxy)chroman-4-carboxylate (14.2 mg, 0.0270 mmol) was dissolved in THF (3 mL) and 1M solution of lithium hydroxide monohydrate in water (54.0 μl, 0.0540 mmol) was added. The mixture was stirred overnight at ambient temperature, then quenched with 4.0 M HCl solution in 1,4-dioxane (20.3 μl, 0.0811 mmol). The reaction mixture was purified on silica gel (MeOH in dichloromethane with 1% acetic acid gradient) to provide 5.1 mg of the title compound as a thin film (37%). MS (apci) m/z=509.7 (M−H).

Workup

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

Sources & evidence

ORD record
ord-6f74a0f7e4dd4c029e81e6fc120f2cb6
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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