Hydrochloric Acid → HCID 44545707, compound

HRID 453399Notes

Reaction equation

HRID 453399 reaction equation
C([O:3][CH2:4][CH2:5][O:6][NH:7][C:8]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][C:18]=1[NH:19][C:20]1[CH:25]=[CH:24][C:23]([I:26])=[CH:22][C:21]=1[F:27])[C:15](=[O:28])[NH:14][CH2:13]2)=[O:9])=C.Cl>CO>[OH:3][CH2:4][CH2:5][O:6][NH:7][C:8]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][C:18]=1[NH:19][C:20]1[CH:25]=[CH:24][C:23]([I:26])=[CH:22][C:21]=1[F:27])[C:15](=[O:28])[NH:14][CH2:13]2)=[O:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86653626HCID 86653626, compound

Product 1

HCID 44545707HCID 44545707, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-(2-fluoro-4-iodo-phenylamino)-1-oxo-2,3-dihydro-1H-isoindole-5-carboxylic acid (2-vinyloxy-ethoxy)-amide (100 mg, 0.20 mmol) in methanol (7 mL) was added hydrochloric acid (1 mL, 1M, 1 mmol). The reaction mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated in vacuo and the resultant residue triturated with hot ethyl acetate. The product was collected by filtration to give the title compound as a pale beige solid (58 mg, 61%). LCMS (Method A): RT=7.64, M+H+=472. 1H NMR (DMSO-d6) 11.89 (1H, s), 9.00 (1H, s), 8.68 (1H, s), 7.68-7.62 (2H, m), 7.49-7.45 (1H, m), 7.24 (1H, s), 7.17 (1H, t, J=8.63 Hz), 4.69 (1H, s), 4.28 (2H, s), 3.89 (2H, t, J=4.82 Hz), 3.58 (2H, t, J=4.73 Hz).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe resultant residue triturated with hot ethyl acetate
  3. filtrationThe product was collected by filtration

Sources & evidence

ORD record
ord-d7a59f5425d54a4885a9d092657fc65d
Source dataset
uspto-grants-2013_07
Patent number
US08492427B2

Reaction notes

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