Hydrochloric Acid → HCID 71667659, compound

HRID 928963Notes

Reaction equation

HRID 928963 reaction equation
[F:1][C:2]1[C:7]2[N:8]=[CH:9][O: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]=[CH:9][O: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 89704805HCID 89704805, compound

Product 1

HCID 71667659HCID 71667659, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 4-fluoro-5-((2-fluoro-4-iodophenyl)amino)-N-(2-(vinyloxy)ethoxy)benzo[d]oxazole-6-carboxamide (598 mg, 1.17 mmol) in CH2Cl2 (5 mL) was added 1.0 N HCl (aq., 6.7 mL, 6.72 mmol) dropwise. After stirring for 1 h, the reaction mixture was treated with saturated NaHCO3 (aq.). The organic layer was washed with water (30 mL×2) 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, 15:1, v/v) and gave the desired product (white solid, 290 mg, 52% yield). 1H NMR (400 MHz, DMSO-d6): δ 11.75 (s, 1H), 8.96 (s, 1H), 8.01 (s, 1H), 7.88 (s, 1H), 7.53 (d, J=9.4 Hz, 1H), 7.28 (d, J=8.7 Hz, 1H), 6.39 (m, 1H), 4.70 (s, 1H), 3.83 (m, 2H), 3.56 (m, 2H). MS (ES+): m/z 476.34 [MH+].

Workup

  1. washThe organic layer was washed with water (30 mL×2) and brine (30 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by column chromatography on silica gel (CH2Cl2/MeOH, 15:1

Sources & evidence

ORD record
ord-84d56b587ee44f508fe5ef412544cc02
Source dataset
uspto-grants-2016_03
Patent number
US09290468B2

Reaction notes

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