Water → HCID 20145052, compound

HRID 1906002Notes

Reaction equation

HRID 1906002 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-e95768c23b314233939d54b28adfe38b
Source dataset
uspto-grants-1987_03
Patent number
US04649146

Reaction notes

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