Hydrochloric Acid → HCID 71665912, compound

HRID 929044Notes

Reaction equation

HRID 929044 reaction equation
[F:1][C:2]1[C:7]2[N:8]=[N:9][S:10][C:6]=2[CH:5]=[C:4]([C:11]([NH:13][O:14][CH2:15][CH2:16][O:17]C=C)=[O:12])[C:3]=1[NH:20][C:21]1[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=1[F:28].Cl.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:1][C:2]1[C:7]2[N:8]=[N:9][S:10][C:6]=2[CH:5]=[C:4]([C:11]([NH:13][O:14][CH2:15][CH2:16][OH:17])=[O:12])[C:3]=1[NH:20][C:21]1[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=1[F:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 89705069HCID 89705069, compound

Product 1

HCID 71665912HCID 71665912, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-fluoro-5-((2-fluoro-4-iodophenyl)amino)-N-(2-(vinyloxy)ethoxy)benzo[d][1,2,3]thiadiazole-6-carboxamide (190 mg, 0.37 mmol) in CH2Cl2 (10 mL) was added 1.0 N HCl (aq., 1.5 mL, 1.5 mmol). After stirring for 1 h, the reaction mixture was neutralized with saturated NaHCO3 (aq.). The aqueous layer was washed with CH2Cl2 (10 mL×2). The combined organic layer was washed with water (30 mL) and brine (30 mL), dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography on silica gel (CH2Cl2/MeOH, 20:1, v/v) and gave the desired product as a yellow solid (154 mg, 84.6% yield). 1H NMR (400 MHz, DMSO-d6): δ 11.88 (s, 1H), 8.65 (s, 1H), 8.52 (s, 1H), 7.36 (d, 1H), 7.25 (d, 1H), 6.42 (d, 1H), 4.69 (m, 1H), 4.05 (m, 2H), 3.80 (m, 2H). MS APCI (+) m/z: m/z 493.2, [M+H].

Workup

  1. washThe aqueous layer was washed with CH2Cl2 (10 mL×2)
  2. washThe combined organic layer was washed with water (30 mL) and brine (30 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography on silica gel (CH2Cl2/MeOH, 20:1

Sources & evidence

ORD record
ord-350ab35cba9d43a9886cd895684af1c7
Source dataset
uspto-grants-2016_03
Patent number
US09290468B2

Reaction notes

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