Hydrochloric Acid → HCID 68701112, compound

HRID 1444637Notes

Reaction equation

HRID 1444637 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:30]([O:32]C)=[O:31])=[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]([CH3:26])[CH2:17][CH:16]([N:27]([CH3:29])[CH3:28])[CH2:15]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].Cl>CO>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:30]([OH:32])=[O:31])=[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]([CH3:26])[CH2:17][CH:16]([N:27]([CH3:28])[CH3:29])[CH2:15]3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68699387HCID 68699387, compound

Product 1

HCID 68701112HCID 68701112, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of methyl 14-cyclohexyl-7-(dimethylamino)-5-methyl-5,6,7,8-tetrahydroindolo[1,2-e][1,5]benzodiazocine-11-carboxylate in MeOH (0.05 M), 40 eq 2N NaOH were added and the reaction stirred at 65° C. for 3 h. The reaction was acidified to pH 2 with HCl and the solvent was evaporated in vacuo. The crude was then purified by prep RP-HPLC (stationary phase: column Waters XTERRA prep. C18, 5 um, 19×150 mm. Mobile phase: acetonitrile/H2O buffered with 0.1% TFA). Fractions containing the pure compound were combined and freeze dried to afford the title compound as a brown powder in 8 % yield (over four steps).

Workup

  1. customthe solvent was evaporated in vacuo
  2. customThe crude was then purified by prep RP-HPLC (stationary phase: column Waters XTERRA prep. C18, 5 um, 19×150 mm. Mobile phase: acetonitrile/H2O buffered with 0.1% TFA)
  3. additionFractions containing the pure compound
  4. customfreeze dried

Sources & evidence

ORD record
ord-59143661d48741f2a57cad87ce9db1b1
Source dataset
uspto-grants-2010_02
Patent number
US07662809B2

Reaction notes

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