Hydrochloric Acid → HCID 21867008, compound

HRID 917028Notes

Reaction equation

HRID 917028 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[C:9]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][C:21]=2[Cl:27])=[C:10]([Cl:18])[C:11]2[N:12]([C:14]([CH3:17])=[N:15][N:16]=2)[CH:13]=1)=[O:7])C.C1COCC1.Cl>[Cl-].[Na+].O.O>[Br:26][C:23]1[CH:24]=[CH:25][C:20]([NH:19][C:9]2[C:8]([C:6]([OH:7])=[O:5])=[CH:13][N:12]3[C:14]([CH3:17])=[N:15][N:16]=[C:11]3[C:10]=2[Cl:18])=[C:21]([Cl:27])[CH:22]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 68862271HCID 68862271, compound

Product 1

HCID 21867008HCID 21867008, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Sodium hydroxide (715 μL of a 1 M solution) was added to a solution of 7-(4-bromo-2-chlorophenylamino)-8-chloro-3-methyl-[1,2,4]triazolo[4,3-a]pyridine-6-carboxylic acid ethyl ester (51a) (79 mg, 179 mmol) in 3:1 THF:water (4.5 mL). After 16 hours, the reaction mixture was poured into a separatory funnel, diluted with brine and acidified with 1 N HCl to about pH 2. The aqueous layer was extracted with 1:1 EtOAc:THF. The combined organic extracts were dried (Na2SO4) and concentrated and the residue (52a) was carried forward without further purification.

Workup

  1. additionthe reaction mixture was poured into a separatory funnel
  2. extractionThe aqueous layer was extracted with 1:1 EtOAc
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated
  5. customthe residue (52a) was carried forward without further purification

Sources & evidence

ORD record
ord-b3ede6332e4f4b30a037d4802f4626e4
Source dataset
uspto-grants-2007_09
Patent number
US07271178B2

Reaction notes

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