Hydrochloric Acid → 5-(Difluoromethyl)-4-(imidazo[1,2-b]pyridazin-3-yl)thiophene-2-carboxylic acid

HRID 2046415Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of methyl 5-(difluoromethyl)-4-(imidazo[1,2-b]pyridazin-3-yl)thiophene-2-carboxylate (57 mg, 0.18 mmol) in methanol (1 mL) and water (0.5 mL) was added NaOH (2 N, 0.28 mL, 0.56 mmol). The mixture was heated to 50° C. for 1 h, cooled to room temperature, and acidified with 1 N HCl. The resultant mixture was concentrated, and used in the next step without further purification. LRMS (APCI) calc'd for (C12H8F2N3O2S) [M+H]+, 296.0. found 296.0.

Workup

temperaturecooled to room temperature
concentrationThe resultant mixture was concentrated
customused in the next step without further purification

Sources & evidence

ORD record: ord-48eb51502afb458ea8184724d4a63591
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592425B2

Reaction notes

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