HCID 59596576, compound → HCID 59596510, compound

HRID 2264970Notes

Reaction equation

HRID 2264970 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]=[N: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>CO.Cl>[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]=[N: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

4

Reactant 1

HCID 59596576HCID 59596576, compound

Product 1

HCID 59596510HCID 59596510, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

To a solution of 7-(2-fluoro-4-iodo-phenylamino)-5-methyl-5H-pyrrolo[3,2-c]pyridazine-6-carboxylic acid (2-vinyloxy-ethoxy)-amide (148 mg, 0.3 mmol) in methanol (5 mL) was added concentrated hydrochloric acid (3 drops) and the reaction mixture stirred at room temperature for 10 minutes. The reaction mixture was concentrated in vacuo and the resultant residue dissolved in acetonitrile/water, neutralised with triethylamine and subjected to reverse-phase HPLC (Phenomenex Luna 5 phenyl/hexyl, 0.1% HCO2H in water on a gradient of acetonitrile 90:10 to 15:85) to give the title compound as an orange solid (82 mg, 52%). LCMS (method A): RT=5.89 min, M+H+=471. 1H NMR (d6-DMSO, 400 MHz) 3.58 (2H, s), 3.91 (2H, s), 3.95 (3H, s), 6.44 (1H, t, J=8.85 Hz), 7.18 (1H, d, J=8.56 Hz), 7.53 (1H, dd, J=11.02, 1.92 Hz), 7.94 (1H, s), 8.43 (1H, d, J=6.27 Hz), 9.31 (1H, d, J=6.52 Hz), 12.09 (1H, s).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe resultant residue dissolved in acetonitrile/water

Sources & evidence

ORD record
ord-b5fa2adc779e4079941420e3bb70cba2
Source dataset
uspto-grants-2010_12
Patent number
US07855216B2

Reaction notes

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