Lithium hydroxide, monohydrate → HCID 90333956, compound

HRID 595596Notes

Reaction equation

HRID 595596 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:36]([CH3:41])[S:37]([CH3:40])(=[O:39])=[O:38])=[CH:21][C:22]6[O:26][C:25]([C:27]([O:29]C)=[O:28])=[C:24]([C:31](=[O:34])[NH:32][CH3:33])[C:23]=6[CH:35]=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.O[Li].O>O1CCOCC1.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:36]([CH3:41])[S:37]([CH3:40])(=[O:39])=[O:38])=[CH:21][C:22]6[O:26][C:25]([C:27]([OH:29])=[O:28])=[C:24]([C:31](=[O:34])[NH:32][CH3:33])[C:23]=6[CH:35]=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 168937Lithium hydroxide, monohydrateHCID 90341055HCID 90341055, compound

Product 1

HCID 90333956HCID 90333956, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a suspension of compound methyl 5-(11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-2-carboxylate (540 mg, 0.93 mmol) in 1,4-dioxane/H2O (6 mL/1 mL) was added LiOH.H2O (196 mg, 4.67 mmol). The mixture was stirred at RT overnight. Then it was concentrated in vacuo, diluted with water, acidized with HCl(aq. 2 M) and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated give the product of compound 5-(11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-2-carboxylic acid (500 mg, yield: 95%). It was used for the next step without further purification. 1H-NMR (DMSO-d6, 400 MHz) δ 9.21 (br s, 1H), 8.17 (s, 1H), 8.11 (s, 1H), 7.69 (d, J=8.4 Hz, 1H), 7.54˜7.58 (m, 1H), 7.49 (d, J=8.4 Hz, 1H), 7.28˜7.11 (m, 2H), 7.07 (s, 1H), 6.95˜6.88 (m, 1H), 6.25 (s, 2H), 3.28 (s., 3H), 2.95 (s, 3H), 2.83 (d, J=4.4 Hz, 3H). MS (M+H)+: 565.

Workup

  1. concentrationThen it was concentrated in vacuo
  2. additiondiluted with water
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ea439b90fdc641bbad65484b7adb2347
Source dataset
uspto-grants-2016_01
Patent number
US09242998B2

Reaction notes

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