Hydrochloric Acid → HCID 24948136, compound

HRID 2264961Notes

Reaction equation

HRID 2264961 reaction equation
C([O:3][CH2:4][CH2:5][O:6][NH:7][C:8]([C:10]1[N:18]([CH3:19])[C:17]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[C:11]=1[NH:20][C:21]1[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=1[F:28])=[O:9])=C.Cl.C(=O)([O-])O.[Na+]>CO>[OH:3][CH2:4][CH2:5][O:6][NH:7][C:8]([C:10]1[N:18]([CH3:19])[C:17]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[C:11]=1[NH:20][C:21]1[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=1[F:28])=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 59596464HCID 59596464, compound

Product 1

HCID 24948136HCID 24948136, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-(2-fluoro-4-iodo-phenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid (2-vinyloxy-ethoxy)-amide (64 mg, 0.13 mmol), 1N aqueous HCl (0.39 mL) and MeOH (4.0 ml) was stirred at room temperature for 20 hours. Sodium hydrogen carbonate (32 mg, 0.39 mmol) was added, stirring was continued for 10 minutes then the reaction mixture was concentrated under reduced pressure. The residue was absorbed onto HM-N and purified by flash chromatography (Si-PPC, dichloromethane:MeOH, gradient 100:0 to 85:15) followed by reversed phase HPLC (Phenomenex Luna 5 phenyl/hexyl, 0.1% TFA in water on a gradient of acetonitrile 95:5 to 50:50) to afford the title compound as a yellow solid (16 mg, 27%). LCMS (method A): RT=5.75 min, M+H+=471. 1H NMR (d4-MeOH, 400 MHz) 8.55 (s, 1H), 8.24 (d, J=6.2 Hz, 1H), 7.52 (d, J=6.2 Hz, 1H), 7.39 (dd, J=10.8 Hz, 1.8 Hz, 1H), 7.14-7.19 (m, 1H), 6.35 (dd, J=8.7 Hz, 8.7 Hz, 1H), 3.94 (s, 3H), 3.88 (t, J=4.5 Hz, 2H), 3.64 (t, J=4.5 Hz, 2H).

Workup

  1. stirringstirring
  2. waitwas continued for 10 minutes
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customThe residue was absorbed onto HM-N
  5. custompurified by flash chromatography (Si-PPC, dichloromethane:MeOH, gradient 100:0 to 85:15)

Sources & evidence

ORD record
ord-2ba10315c76f4c89b770241cd2d6dd5a
Source dataset
uspto-grants-2010_12
Patent number
US07855216B2

Reaction notes

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