Sodium Hydroxide → 1-[5-(2-Ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-ylmethyl)thiophen-2-yl]cyclopent-3-ene carboxylic acid

HRID 481391Notes

Reaction equation

C([O:3][C:4]([C:6]1([C:11]2[S:12][C:13]([CH2:16][N:17]3[C:21]4=[N:22][C:23]([CH3:27])=[CH:24][C:25]([CH3:26])=[C:20]4[N:19]=[C:18]3[CH2:28][CH3:29])=[CH:14][CH:15]=2)[CH2:10][CH:9]=[CH:8][CH2:7]1)=[O:5])C.[OH-].[Na+]>CO>[CH2:28]([C:18]1[N:17]([CH2:16][C:13]2[S:12][C:11]([C:6]3([C:4]([OH:5])=[O:3])[CH2:10][CH:9]=[CH:8][CH2:7]3)=[CH:15][CH:14]=2)[C:21]2=[N:22][C:23]([CH3:27])=[CH:24][C:25]([CH3:26])=[C:20]2[N:19]=1)[CH3:29]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of the product of Step 5, above (6), in methanol was added an excess of 2N NaOH. The reaction mixture was heated to 80° C. for 1 hour, cooled to room temperature and the solvent evaporated. Water was added to the residue and the solution was extracted 2 times with EtOAc. The aqueous layer was acidified with 10% HCl and the resultant white suspension was extracted 2 times with EtOAc. The organics were dried over MgSO4, filtered and concentrated to a solid. The solid was crystallized from EtOAc to yield the title compound (8).

Workup

temperaturecooled to room temperature
customthe solvent evaporated
additionWater was added to the residue
extractionthe solution was extracted 2 times with EtOAc
extractionthe resultant white suspension was extracted 2 times with EtOAc
dry with materialThe organics were dried over MgSO4
filtrationfiltered
concentrationconcentrated to a solid
customThe solid was crystallized from EtOAc

Sources & evidence

ORD record: ord-9031c5cc868a412a889a909539eeb33c
Source dataset: uspto-grants-1998_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05789415

Reaction notes

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