Methanol → HCID 11597476, compound

HRID 1444632Notes

Reaction equation

HRID 1444632 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:32]([O:34]C)=[O:33])=[CH:12][C:13]=3[N:14]3[C:21]=2[C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[N:18]([CH2:26][CH2:27][N:28]([CH3:30])[CH3:29])[C:17](=O)[CH2:16][CH2:15]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(C)C.CO.[OH-].[Na+]>C1COCC1>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:32]([OH:34])=[O:33])=[CH:12][C:13]=3[N:14]3[C:21]=2[C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[N:18]([CH2:26][CH2:27][N:28]([CH3:30])[CH3:29])[CH2:17][CH2:16][CH2:15]3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 887MethanolHCID 1068Dimethyl SulfideHCID 14798Sodium HydroxideHCID 68699389Methyl 14-cyclohexyl-5-[2-(dimethylamino)ethyl]-6-oxo-5,6,7,8-tetrahydroindolo[1,2-e][1,5]benzodiazocine-11-carboxylate

Product 1

HCID 11597476HCID 11597476, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 14-cyclohexyl-5-[2-(dimethylamino)ethyl]-6-oxo-5,6,7,8-tetrahydroindolo[1,2-e][1,5]benzodiazocine-11-carboxylate (prepared as described in Example 8, Step 7) in THF (0.1 M), BH3.Me2S (20 eq, 2 M solution in THF) was added. The solution was stirred overnight at RT. MeOH was carefully added to the mixture to quench the reaction, followed by an excess of 1 N NaOH (>10 eq). The mixture was heated at 60° C. for 12 h. The solvent was evaporated in vacuo. The crude was then purified by prep RP-HPLC (stationary phase: column Waters XTERRA prep. C18, 5 um, 19×100 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 (24% over three steps).

Workup

  1. customto quench
  2. customthe reaction
  3. temperatureThe mixture was heated at 60° C. for 12 h
  4. customThe solvent was evaporated in vacuo
  5. customThe crude was then purified by prep RP-HPLC (stationary phase: column Waters XTERRA prep. C18, 5 um, 19×100 mm. Mobile phase: MeCN/H2O buffered with 0.1% TFA)
  6. additionFractions containing the pure compound
  7. customfreeze dried

Sources & evidence

ORD record
ord-ca76a5a6b2854a68855dedfe03b4643b
Source dataset
uspto-grants-2010_02
Patent number
US07662809B2

Reaction notes

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