Water → HCID 68506952, compound

HRID 1714053Notes

Reaction equation

HRID 1714053 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:34]([O:36]C)=[O:35])=[CH:12][C:13]=3[N:14]3[CH2:21][CH2:20][N:19]([CH2:22][C@H:23]4[CH2:27][CH2:26][CH2:25][N:24]4[CH3:28])[CH2:18][C:17]4[CH:29]=[C:30]([F:33])[CH:31]=[CH:32][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.[OH-].[K+]>O1CCOCC1>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:34]([OH:36])=[O:35])=[CH:12][C:13]=3[N:14]3[CH2:21][CH2:20][N:19]([CH2:22][C@H:23]4[CH2:27][CH2:26][CH2:25][N:24]4[CH3:28])[CH2:18][C:17]4[CH:29]=[C:30]([F:33])[CH:31]=[CH:32][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 68501783HCID 68501783, compound

Product 1

HCID 68506952HCID 68506952, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 14-cyclohexyl-3-fluoro-6-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocine-11-carboxylate was dissolved in a solution of dioxane: H2O 2O (1:1) (0.1 M) and to that solution aqueous KOH (3 eq, 5 N) was added. The solution was stirred at 60° C. for 3 h. The solvent was evaporated in vacuo. The crude was then purified by automated RP-MS-HPLC (stationary phase: column Waters SYMMETRY prep. C18, 7 μm, 19×300 mm. Mobile phase: MeCN/H2O buffered with 0.1% TFA). Fractions containing the pure compound were combined and freeze dried to afford the title compound as a white powder (18%).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customThe crude was then purified by automated RP-MS-HPLC (stationary phase: column Waters SYMMETRY prep. C18, 7 μm, 19×300 mm. Mobile phase: MeCN/H2O buffered with 0.1% TFA)
  3. additionFractions containing the pure compound
  4. customfreeze dried

Sources & evidence

ORD record
ord-7af92b206fe14263a9c3efd7b77a5ac5
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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