Dichloromethane → (E)-3-(2-Oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-6-yl)acrylic acid hydrochloride

HRID 83032

Reaction equation

HRID 83032 reaction equation
FC(F)(F)C(O)=O.[O:8]=[C:9]1[NH:26][C:12]2=[N:13][CH:14]=[C:15](/[CH:17]=[CH:18]/[C:19]([O:21]C(C)(C)C)=[O:20])[CH:16]=[C:11]2[NH:10]1.[Cl:27]CCl>>[ClH:27].[O:8]=[C:9]1[NH:26][C:12]2=[N:13][CH:14]=[C:15](/[CH:17]=[CH:18]/[C:19]([OH:21])=[O:20])[CH:16]=[C:11]2[NH:10]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 68338066(E)-tert-butyl 3-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-6-yl)acrylate

Product 1

HCID 70926863(E)-3-(2-Oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-6-yl)acrylic acid hydrochloride

Procedure

Trifluoroacetic acid (2 mL) was added to a suspension of (E)-tert-butyl 3-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-6-yl)acrylate (400 mg, 1.54 mmol) in dichloromethane (2 mL) at room temperature. The reaction mixture was stirred for 1 hour then concentrated to dryness. The resulting residue was suspended in a solution of hydrochloric acid in dioxane 4N (2 mL). After 10 minutes stirring at room temperature, the precipitate was filtered and washed with diethyl ether to afford the title product as a pale yellow solid (381 mg, quantitative).

Workup

  1. concentrationthen concentrated to dryness
  2. stirringAfter 10 minutes stirring at room temperature
  3. filtrationthe precipitate was filtered
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-8db42b6817374918a216ec71de8f61c2
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Linked notes

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