Hydrochloric Acid → HCID 90403914, compound

HRID 1468976Notes

Reaction equation

HRID 1468976 reaction equation
[OH-].[Na+].[NH2:3][C:4]1[C:9]([F:10])=[C:8]([C:11]2[CH:19]=[CH:18][C:14]3=[N:15][O:16][N:17]=[C:13]3[CH:12]=2)[N:7]=[C:6]([C:20]([O:22]C)=[O:21])[C:5]=1[Cl:24].Cl>CO>[NH2:3][C:4]1[C:9]([F:10])=[C:8]([C:11]2[CH:19]=[CH:18][C:14]3=[N:15][O:16][N:17]=[C:13]3[CH:12]=2)[N:7]=[C:6]([C:20]([OH:22])=[O:21])[C:5]=1[Cl:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 90403870HCID 90403870, compound

Product 1

HCID 90403914HCID 90403914, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
23 °C

Procedure

A 2M solution of aqueous sodium hydroxide (620 microliters (μL), 1.2 mmol) was added to a stirred suspension of methyl 4-amino-6-(benzo[c][1,2,5]oxadiazol-5-yl)-3-chloro-5-fluoropicolinate (200 mg, 0.62 mmol) in methanol (1.3 mL) at 23° C. The heterogeneous light brown mixture was stirred at 23° C. for 72 h. The reaction mixture was adjusted to approximately pH=4 via dropwise addition of concentrated hydrochloric acid and concentrated via rotary evaporation. The residue was slurried in water and vacuum filtered to afford the title compound (120 mg, 63% yield).

Workup

  1. concentrationconcentrated via rotary evaporation
  2. filtrationvacuum filtered

Sources & evidence

ORD record
ord-8a127cf0361f40cdab1925bbadc908f2
Source dataset
uspto-grants-2015_04
Patent number
US09006250B2

Reaction notes

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