Hydrochloric Acid → HCID 15684577, compound

HRID 728151Notes

Reaction equation

HRID 728151 reaction equation
O[C:2]1[CH:3]=[C:4]([CH2:13][CH2:14][C:15]2[N:16]=[C:17]3[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][N:18]3[C:25]=2[CH3:26])[CH:5]=[CH:6][C:7]=1[NH:8][C:9]([NH:11][CH3:12])=[O:10].C(OCC)(=O)C.Cl.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:24][O:23][C:21]1[CH:20]=[CH:19][N:18]2[C:25]([CH3:26])=[C:15]([CH2:14][CH2:13][C:4]3[CH:5]=[CH:6][C:7]4[N:8]=[C:9]([NH:11][CH3:12])[O:10][C:2]=4[CH:3]=3)[N:16]=[C:17]2[CH:22]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 15684663HCID 15684663, compound

Product 1

HCID 15684577HCID 15684577, compoundYield 14.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2-[2-{3-hydroxy-4-(3-methylureido)phenyl}ethyl]-7-methoxy-3-methylimidazo[1,2-a]pyridine (1.9 g) and polyphosphate ester (15 g) was stirred for 1.5 hours at 130° C. To the reaction mixture was added a mixture of ethyl acetate and water, and the mixture was adjusted to pH 1 with 6N hydrochloric acid. The separated aqueous layer was adjusted to pH 8 with aqueous potassium carbonate solution. The aqueous mixture was extracted with a mixture of ethyl acetate and tetrahydrofuran with salting-out technique. The extract was washed with brine and dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was triturated with a mixture of diethyl ether and ethyl acetate, and the resulting precipitate was crystallized from a mixture of methanol, ethyl acetate and isopropyl ether to give 6-[2-(7-methoxy-3-methylimidazo[1,2-a]pyridin-2-yl)ethyl]-2-methylaminobenzoxazole (0.26 g).

Workup

  1. additionTo the reaction mixture was added
  2. extractionThe aqueous mixture was extracted with a mixture of ethyl acetate and tetrahydrofuran with salting-out technique
  3. washThe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent
  6. customgave a residue, which
  7. customwas triturated with a mixture of diethyl ether and ethyl acetate
  8. customthe resulting precipitate was crystallized from a mixture of methanol, ethyl acetate and isopropyl ether

Sources & evidence

ORD record
ord-d5e78d284ca04718a60c3daf8d1d10e3
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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