Hydrochloric Acid → HCID 67288840, compound

HRID 1626399Notes

Reaction equation

HRID 1626399 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[Li].O.O.Cl>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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 67287030HCID 67287030, compound

Product 1

HCID 67288840HCID 67288840, compoundYield 54.1%

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, 0.096 mmol), LiOH—H2O-1M−H2O (191.5 μL, 0.1915 mmol), and THF (1.5 mL) was stirred at ambient temperature for 3 days. The mixture was quenched with HCl (4M in dioxane) (71.83 μL, 0.287 mmol). The crude material was purified by silica gel column chromatography to provide the desired product (0.027 g). MS (APCI)=520.2 (M+1).

Workup

  1. customThe crude material was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-63fd4032726f4951b489b559f8abeed1
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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