Hydrochloric Acid → Gdc-0623

HRID 2064017Notes

Reaction equation

HRID 2064017 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]([I: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]([I:23])=[CH:19][C:18]=1[F:24])=[O:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 591401665-(2-Fluoro-4-iodophenylamino)-imidazo[1,5-a]pyridine-6-carboxylic acid (2-vinyloxyethoxy)-amide

Product 1

HCID 42642654Gdc-0623Yield 92.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 5-(2-fluoro-4-iodophenylamino)-imidazo[1,5-a]pyridine-6-carboxylic acid (2-vinyloxyethoxy)-amide (2.87 g, 5.95 mmol) in methanol (45 mL) was added aqueous hydrochloric acid (11.9 mL, 1M, 11.9 mmol). The reaction mixture was stirred at room temperature for 45 minutes during which time the solids dissolved. The reaction mixture was concentrated in vacuo to remove the methanol. The resultant solution was diluted with 1:1 tert-butylmethylether:ethyl acetate (20 mL) and aqueous saturated sodium hydrogen carbonate solution (20 mL) added. The resultant mixture was sonicated until a precipitate formed and the precipitate was collected by filtration and dried in vacuo at 45° C. to yield the title compound as a yellow solid (2.5 g, 92%). LCMS (Method A): RT=5.58 min, M+H+=457. 1H NMR (DMSO-d6, 400 MHz) 8.05 (1 H, s), 7.58 (1 H, dd, J=10.69, 1.92 Hz), 7.43 (1 H, s), 7.39 (1 H, d, J=9.33 Hz), 7.31-7.28 (1 H, m), 6.89 (1 H, d, J=9.31 Hz), 6.34 (1 H, t, J=8.68 Hz), 4.64 (1 H, s), 3.64 (2 H, t, J=4.78 Hz), 3.46 (2 H, m).

Workup

  1. dissolutiondissolved
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto remove the methanol
  4. additionThe resultant solution was diluted with 1:1 tert-butylmethylether
  5. additionethyl acetate (20 mL) and aqueous saturated sodium hydrogen carbonate solution (20 mL) added
  6. customThe resultant mixture was sonicated until a precipitate
  7. customformed
  8. filtrationthe precipitate was collected by filtration
  9. customdried in vacuo at 45° C.

Sources & evidence

ORD record
ord-adc6da663b054512bb11dd9f4f6160f5
Source dataset
uspto-grants-2012_10
Patent number
US08288408B2

Reaction notes

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