Hydrochloric Acid → HCID 11568276, compound

HRID 1714068Notes

Reaction equation

HRID 1714068 reaction equation
[CH:1]1([C:7]2[C:15]3[CH:14]=[CH:13][C:12]([C:16]([O:18]C)=[O:17])=[CH:11][C:10]=3[N:9]3[CH2:20][CH2:21][N:22]([CH2:29][CH2:30][N:31]([CH3:33])[CH3:32])[CH2:23][C:24]4[CH:28]=[CH:27][O:26][C:25]=4[C:8]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].Cl>CO>[CH:1]1([C:7]2[C:15]3[CH:14]=[CH:13][C:12]([C:16]([OH:18])=[O:17])=[CH:11][C:10]=3[N:9]3[CH2:20][CH2:21][N:22]([CH2:29][CH2:30][N:31]([CH3:33])[CH3:32])[CH2:23][C:24]4[CH:28]=[CH:27][O:26][C:25]=4[C:8]=23)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68506720HCID 68506720, compound

Product 1

HCID 11568276HCID 11568276, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 13-cyclohexyl-5-[2-(dimethylamino)ethyl]-4,5,6,7-tetrahydrofuro[3′,2′:6,7][1,4]diazocino[1,8-a]indole-10-carboxylate in MeOH (0.07 M), 15 eq 1N NaOH was added. The solution was stirred at 70° C. for 6 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: MeCN/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 two 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: MeCN/H2O buffered with 0.1% TFA)
  3. additionFractions containing the pure compound
  4. customfreeze dried

Sources & evidence

ORD record
ord-40b06768e2aa4efc9ccdcc183e624a65
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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