Hydrochloric Acid → HCID 68861079, compound

HRID 494727Notes

Reaction equation

HRID 494727 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1[C:8]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([Br:34])=[CH:30][C:29]=2[Cl:35])=[C:9]([Cl:26])[C:10]2[N:11]([C:13]([CH2:16][NH:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:14][N:15]=2)[CH:12]=1)=[O:6].CO.O.Cl>O>[Br:34][C:31]1[CH:32]=[CH:33][C:28]([NH:27][C:8]2[C:7]([C:5]([OH:6])=[O:4])=[CH:12][N:11]3[C:13]([CH2:16][NH:17][CH2:18][C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])=[CH:14][N:15]=[C:10]3[C:9]=2[Cl:26])=[C:29]([Cl:35])[CH:30]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22242641Methanol--water (1/1)HCID 68859552HCID 68859552, compound

Product 1

HCID 68861079HCID 68861079, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydroxide (1.0 M aqueous solution, 0.16 mL, 0.16 mmol) was added to a solution of 7-(4-bromo-2-chlorophenylamino)-3-[(tert-butoxycarbonylmethylamino)-methyl]-8-chloroimidazo[1,2-a]pyridine-6-carboxylic acid methyl ester (60) (15 mg, 0.026 mmol) in 4:1 MeOH/water (5 mL). When the reaction was complete, the solution was diluted with water, acidified to pH 3 by addition of 1.0 M aqueous HCl, and extracted with ethyl acetate. The organic extracts were dried over NaSO4, filtered, concentrated in vacuo to provide the desired product as a white crystalline solid (12 mg, 84%). MS (APCI−) m/z 541, 543, 545 (M-; Cl, Br pattern) detected.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic extracts were dried over NaSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4dd69016d4874fd4b880d62c774585af
Source dataset
uspto-grants-2009_05
Patent number
US07538120B2

Reaction notes

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