Acetic Acid Mixture with Hydrobromic Acid → HCID 90341045, compound

HRID 595560Notes

Reaction equation

HRID 595560 reaction equation
[F:1][C:2]1[C:3]2[CH:4]=[C:5]3[C:14]4[N:15]=[C:16]([C:19]5[C:20]([N:40]([CH3:45])[S:41]([CH3:44])(=[O:43])=[O:42])=[CH:21][C:22]6[O:26][C:25]([C:27]7[CH:28]=[N:29][C:30]([O:33]C)=[CH:31][CH:32]=7)=[C:24]([C:35]([NH:37][CH3:38])=[O:36])[C:23]=6[CH:39]=5)[CH:17]=[CH:18][C:13]=4[O:12][CH2:11][N:6]3[C:7]=2[CH:8]=[CH:9][CH:10]=1.Br.CC(O)=O>CC(O)=O>[F:1][C:2]1[C:3]2[CH:4]=[C:5]3[C:14]4[N:15]=[C:16]([C:19]5[C:20]([N:40]([CH3:45])[S:41]([CH3:44])(=[O:43])=[O:42])=[CH:21][C:22]6[O:26][C:25]([C:27]7[CH:32]=[CH:31][C:30](=[O:33])[NH:29][CH:28]=7)=[C:24]([C:35]([NH:37][CH3:38])=[O:36])[C:23]=6[CH:39]=5)[CH:17]=[CH:18][C:13]=4[O:12][CH2:11][N:6]3[C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 778453345-(11-fluoro-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indol-2-yl)-2-(6-methoxypyridin-3-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

Product 1

HCID 90341045HCID 90341045, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-(11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)-2-(6-methoxypyridin-3-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (40 mg, 0.64 mmol) in HOAc (4 mL) was added HBr—HOAc (4 ml) at 0° C. Then the mixture was stirred at 80° C. for 2 hours. After the solvent was removed by vacuum, the residue was washed with Na2CO3 (a.q.), extracted with DCM, dried over Na2SO4, filtrated and concentrated in vacuo. The residue was purified by prep-HPLC to give the product 5-(11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)-N-methyl-6-(N-methylmethylsulfonamido)-2-(6-oxo-1,6-dihydropyridin-3-yl)benzofuran-3-carboxamide (20 mg, yield: 50%). 1H-NMR (MeOD, 400 MHz) δ 8.33 (s, 1H), 7.96 (q, J=9.6 Hz, 1H), 7.84 (s, 1H), 7.88 (s, 1H), 7.55 (d, J=9.6 Hz, 2H), 7.28 (d, J=9.6 Hz, 1H), 7.15˜7.21 (m, 2H), 6.87 (q, J=9.6 Hz, 1H), 6.53 (t, J=9.6 Hz, 1H), 6.06 (s, 2H), 3.31 (s, 3H), 2.95 (d, J=9.6 Hz, 3H), 2.85 (s, 3H). MS (M+H)+: 614.

Workup

  1. customAfter the solvent was removed by vacuum
  2. washthe residue was washed with Na2CO3 (a.q.)
  3. extractionextracted with DCM
  4. dry with materialdried over Na2SO4
  5. filtrationfiltrated
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-15ddf713935e487194e55bb7d76a8387
Source dataset
uspto-grants-2016_01
Patent number
US09242998B2

Reaction notes

Loading…