Hydrochloric Acid → 5-(4-Bromo-2-fluorophenylamino)-imidazo[1,5-a]pyridine-6-carboxylic acid (2-hydroxyethoxy)-amide

HRID 1500718Notes

Reaction equation

HRID 1500718 reaction equation
C([O:3][CH2:4][CH2:5][O:6][NH:7][C:8]([C:10]1[CH:11]=[CH:12][C:13]2[N:14]([CH:25]=[N:26][CH:27]=2)[C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][C:18]=1[F:24])=[O:9])=C.Cl>CO>[OH:3][CH2:4][CH2:5][O:6][NH:7][C:8]([C:10]1[CH:11]=[CH:12][C:13]2[N:14]([CH:25]=[N:26][CH:27]=2)[C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][C:18]=1[F:24])=[O:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59140113HCID 59140113, compound

Product 1

HCID 441379355-(4-Bromo-2-fluorophenylamino)-imidazo[1,5-a]pyridine-6-carboxylic acid (2-hydroxyethoxy)-amideYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 5-(4-Bromo-2-fluorophenylamino)-imidazo[1,5-a]pyridine-6-carboxylic acid (2-vinyloxyethoxy)-amide (1.33 g, 3.05 mmol) in methanol (40 mL) was added aqueous hydrochloric acid (6.7 mL, 1M, 6.7 mmol). The reaction mixture was stirred at room temperature for 30 minutes then concentrated in vacuo to remove the methanol. The resultant residue was dissolved in 1:1 diethylether:ethyl acetate (30 mL) and aqueous saturated sodium hydrogen carbonate solution (30 mL) added. The resultant mixture was sonicated until a precipitate formed, the precipitate collected by filtration and washed with water then diethyl ether to yield the title compound as a yellow solid (1.12 g, 90%). LCMS (method A): RT=5.22 min, [M+H]+=409/411. 1H NMR (DMSO-d6, 400 MHz) 9.20 (1 H, s), 8.07 (1 H, s), 7.51 (1 H, dd, J=10.86, 2.22 Hz), 7.44 (1 H, s), 7.40 (1 H, d, J=9.33 Hz), 7.16 (1 H, ddd, J=8.61, 2.20, 1.07 Hz), 6.89 (1 H, d, J=9.31 Hz), 6.50 (1 H, t, J=8.84 Hz), 4.63 (1 H, s), 3.65 (2 H, t, J=4.79 Hz), 3.46 (3 H, s).

Workup

  1. concentrationthen concentrated in vacuo
  2. customto remove the methanol
  3. dissolutionThe resultant residue was dissolved in 1:1 diethylether
  4. additionethyl acetate (30 mL) and aqueous saturated sodium hydrogen carbonate solution (30 mL) added
  5. customThe resultant mixture was sonicated until a precipitate
  6. customformed
  7. filtrationthe precipitate collected by filtration
  8. washwashed with water

Sources & evidence

ORD record
ord-a195dbe9b04540a19f7ccedfcd498444
Source dataset
uspto-grants-2015_12
Patent number
US09206174B2

Reaction notes

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