Hydrochloric Acid → HCID 68505284, compound

HRID 1714031Notes

Reaction equation

HRID 1714031 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:12]3=[C:13]([CH:24]4[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]4)[C:14]4[CH:15]=[CH:16][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:19]=4[N:11]3[CH2:10][C:9](=O)[N:8]([CH2:31][CH2:32][N:33]([CH3:35])[CH3:34])[CH2:7][C:6]=2[CH:36]=1.B.C1COCC1.Cl>C1COCC1.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:12]3=[C:13]([CH:24]4[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]4)[C:14]4[CH:15]=[CH:16][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:19]=4[N:11]3[CH2:10][CH2:9][N:8]([CH2:31][CH2:32][N:33]([CH3:35])[CH3:34])[CH2:7][C:6]=2[CH:36]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 68508758HCID 68508758, compound

Product 1

HCID 68505284HCID 68505284, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-chloro-14-cyclohexyl-6-[2-(dimethylamino)ethyl]-7-oxo-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocine-11-carboxylate (from Step 6) in THF (0.02 M), BH3.THF (1 M solution in THF, 5 eq) was added and the solution allowed to stir at RT for 2 h. MeOH (0.02 M) and a 1.25 M solution HCl in MeOH (0.24 M) were added carefully and stirred overnight at RT before being heated at 60° C. for 3 h. The volatiles were then removed in vacuo. The volume of the solution was reduced in vacuo before diluting with EtOAc. The organic phase was washed with saturated aqueous NaHCO3 and brine. The organic phase was dried over Na2SO4, filtered and the solvent evaporated in vacuo to afford the title compound. The crude was then used in the next step without any further purification (quant); MS (ES+) 494 (M+H)+.

Workup

  1. stirringstirred overnight at RT
  2. temperaturebefore being heated at 60° C. for 3 h
  3. customThe volatiles were then removed in vacuo
  4. additionbefore diluting with EtOAc
  5. washThe organic phase was washed with saturated aqueous NaHCO3 and brine
  6. dry with materialThe organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-1c81a3ac347f4bf29395b7c5dfcd80a8
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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