Trifluoroacetic acid → 4-Fluoro-2-oxo-1-(4-piperidinyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridine

HRID 1671585Notes

Reaction equation

HRID 1671585 reaction equation
F[C:2]1[CH:3]=[C:4]2[N:10]([CH:11]3[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]3)[C:9](=[O:24])[NH:8][C:5]2=[N:6][CH:7]=1.[F:25]C(F)(F)C(O)=O>ClCCl>[F:25][N:6]1[CH:7]=[CH:2][CH:3]=[C:4]2[N:10]([CH:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[C:9](=[O:24])[NH:8][CH:5]12

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22293159tert-Butyl 4-(6-fluoro-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate

Product 1

HCID 865950294-Fluoro-2-oxo-1-(4-piperidinyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(6-fluoro-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate (340 mg, 1.01 mmol) was dissolved in dichloromethane (5 mL) and trifluoroacetic acid (5 mL) was added. After 2 h, the reaction was concentrated, diluted with dichlormethane (5 mL) and a solution of 1 N hydrochloric acid in 1,4-dioxane (2 mL) was added at room temperature. Concentration afforded the title compound (302 mg). MS 237.2 (M+1) 1H NMR (500 MHz, CD3OD) δ 7.92 (br s, 1H), 7.70 (dd, 1H), 4.60 (m, 1H), 3.60 (s, 2H), 3.25 (dd, 2H), 2.70 (m, 2H), 2.10 (d, 2H).

Workup

  1. concentrationthe reaction was concentrated
  2. additiondiluted with dichlormethane (5 mL)
  3. additiona solution of 1 N hydrochloric acid in 1,4-dioxane (2 mL) was added at room temperature
  4. concentrationConcentration

Sources & evidence

ORD record
ord-75e13532e5ee43a28af35c988b4ff778
Source dataset
uspto-grants-2011_08
Patent number
US07994325B2

Reaction notes

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