Hydrochloric Acid → HCID 52934784, compound

HRID 1259373Notes

Reaction equation

HRID 1259373 reaction equation
Cl.C(OC([N:9]1[C:13]2=[C:14]([NH:29][S:30]([C:33]3([CH2:36][CH:37]([OH:40])[CH2:38][OH:39])[CH2:35][CH2:34]3)(=[O:32])=[O:31])[C:15]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][C:22]=3[F:28])=[C:16]([CH3:19])[C:17](=[O:18])[N:12]2[CH2:11][CH2:10]1)=O)(C)(C)C.CO>C1COCC1.C(Cl)(Cl)Cl>[Br:27][C:24]1[CH:25]=[CH:26][C:21]([NH:20][C:15]2[C:14]([NH:29][S:30]([C:33]3([CH2:36][CH:37]([OH:40])[CH2:38][OH:39])[CH2:34][CH2:35]3)(=[O:32])=[O:31])=[C:13]3[NH:9][CH2:10][CH2:11][N:12]3[C:17](=[O:18])[C:16]=2[CH3:19])=[C:22]([F:28])[CH:23]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 67194147HCID 67194147, compound

Product 1

HCID 52934784HCID 52934784, compoundYield 39.6%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

Concentrated HCl (3 mL) was added to a stirred solution of 7-(4-bromo-2-fluoro-phenylamino)-8-[1-(2,3-dihydroxy-propyl)-cyclopropanesulfonylamino]-6-methyl-5-oxo-2,3-dihydro-5H-imidazo[1,2-a]pyridine-1-carboxylic acid tert-butyl ester (75 mg) in THF (10 mL). The resulting mixture was stirred at 45° C. for 1 hour. The reaction was monitored by TLC (10% MeOH in CHCl3). The reaction mixture was concentrated and partitioned between ethyl acetate and water. The organic layer was washed with saturated NaHCO3 solution and concentrated to afford 25 mg of the product (39.58% yield).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between ethyl acetate and water
  3. washThe organic layer was washed with saturated NaHCO3 solution
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-dba8b08320424506b87d16b631e03698
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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