Water → HCID 20145052, compound

HRID 648583Notes

Reaction equation

HRID 648583 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:12]2[N:13]=[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]3[CH:20]=2)=[C:5]([C:7]([O:9][CH2:10][CH3:11])=O)[N:6]=1.[BrH:21].[NH+]1C=CC=C[CH:23]=1.[OH2:28].C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C.O1CCCC1.C(OCC)(=O)C>[NH2:1][C:2]1[S:3][C:4]([C:12]2[N:13]=[C:14]3[CH:19]=[C:18]([CH3:23])[CH:17]=[CH:16][N:15]3[C:20]=2[Br:21])=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:28])[N:6]=1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 20145005HCID 20145005, compoundHCID 21226041Pyridinium hydrobromide

Product 1

HCID 20145052HCID 20145052, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-(2-amino-4-ethoxycarbonyl-5-thiazolyl)imidazo[1,2-a]pyridine (3.0 g) in acetic acid (20 ml) was added pyridinium hydrobromide perbromide (3.5 g) at ambient temperature with stirring, which was continued under the same condition for 30 minutes. The reaction mixture was poured into a mixture of water, ethyl acetate and tetrahydrofuran and the resultant mixture was adjusted to pH 7.5 with 20% potassium carbonate. The separated organic layer was washed with brine and dried over magnesium sulfate. The solvent was removed in vacuo and the residue was recrystallized from a mixture of ethyl acetate and tetrahydrofuran to give 2-(2-amino-4-ethoxycarbonyl-5-thiazolyl)-3-bromo-7-methylimidazo[1,2-a]pyridine (3.0 g). mp 127°-129° C. (dec.).

Workup

  1. washThe separated organic layer was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was removed in vacuo
  4. customthe residue was recrystallized from a mixture of ethyl acetate and tetrahydrofuran

Sources & evidence

ORD record
ord-15d8fd8fc5ac4cba90d2d5ae7e3aa9c3
Source dataset
uspto-grants-1988_04
Patent number
US04735957

Reaction notes

Loading…