Acetic Acid → 4-Amino-3,6-dimethyl-2-(3-pyridinyl)thieno[2,3-b]pyridine-5-carboxylic acid

HRID 573558Notes

Reaction equation

[NH2:1][C:2]1[C:7]([C:8]([O:10]CC)=[O:9])=[C:6]([CH3:13])[N:5]=[C:4]2[S:14][C:15]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)=[C:16]([CH3:17])[C:3]=12.[OH-].[Na+].C(O)(=O)C>CS(C)=O.O>[NH2:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([CH3:13])[N:5]=[C:4]2[S:14][C:15]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)=[C:16]([CH3:17])[C:3]=12

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of ethyl 4-amino-3,6-dimethyl-2-(3-pyridinyl)thieno[2,3-b]pyridine-5-carboxylate (120 mg, 0.367 mmol) (Description 32) in DMSO (3 mL) and 2M NaOH (0.916 mL, 1.833 mmol) was heated at 120° C. for 1 h. After cooling to RT, the mixture was diluted with water (20 mL), acidified with acetic acid to pH 6. The mixture was extracted with 10% MeOH in DCM (5×30 mL). The combined organics were dried and concentrated. The residue was passed through a C18 solid phase extractor cartridge, eluted with water (4×30 mL) followed by MeOH (4×30 mL). The combined organics were concentrated and dried at 55° C. in a vacuum oven, to afford the title compound (98 mg). LCMS (A) m/z: 300 [M+1]+, Rt 0.58 min (acidic).

Workup

temperatureAfter cooling to RT
extractionThe mixture was extracted with 10% MeOH in DCM (5×30 mL)
customThe combined organics were dried
concentrationconcentrated
washeluted with water (4×30 mL)
concentrationThe combined organics were concentrated
customdried at 55° C. in a vacuum oven

Sources & evidence

ORD record: ord-d1d3efd1d6f0434b8a02ed6c53ceaee6
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029545B2

Reaction notes

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