Acetic Acid → methyl 14-cyclohexyl-6-[(1-methyl-1H-pyrazol-4-yl)methyl]-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocine-11-carboxylate

HRID 1714059Notes

Reaction equation

HRID 1714059 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:26]([O:28][CH3:29])=[O:27])=[CH:12][C:13]=3[N:14]3[CH2:21][CH2:20][NH:19][CH2:18][C:17]4[CH:22]=[CH:23][CH:24]=[CH:25][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:30][N:31]1[CH:35]=[C:34]([CH:36]=O)[CH:33]=[N:32]1.C(O)(=O)C.[BH3-]C#N.[Na+]>CO>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:26]([O:28][CH3:29])=[O:27])=[CH:12][C:13]=3[N:14]3[CH2:21][CH2:20][N:19]([CH2:36][C:34]4[CH:33]=[N:32][N:31]([CH3:30])[CH:35]=4)[CH2:18][C:17]4[CH:22]=[CH:23][CH:24]=[CH:25][C:16]=4[C:15]=23)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5731171-Methyl-1H-pyrazole-4-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 68505807Methyl 14-cyclohexyl-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocine-11-carboxylate

Product 1

HCID 68506634methyl 14-cyclohexyl-6-[(1-methyl-1H-pyrazol-4-yl)methyl]-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocine-11-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 14-cyclohexyl-5,6,7,8-tetrahydroindolo[2,1-a][2,5]-benzodiazocine-11-carboxylate (prepared as described in Example 48, Step 3) in MeOH (0.06 M), 1-methyl-1H-pyrazole-4-carbaldehyde (3 eq) was added and the pH adjusted to pH 4 with acetic acid. The solution was stirred at RT for 30 mins before addition of NaBH3CN (1.5 eq). The reaction was stirred at RT for 16 h. The reaction was quenched with saturated aqueous NaHCO3 and extracted with EtOAc (×2). The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to give the title compound as a viscous oil (quantitative); MS (ES+) m/z 483 (M+H)+

Workup

  1. customThe reaction was quenched with saturated aqueous NaHCO3
  2. extractionextracted with EtOAc (×2)
  3. washThe combined organics were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f3ef80f66de1449896f317c82f587198
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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