Potassium Hydroxide → HCID 69181078, compound

HRID 497367Notes

Reaction equation

HRID 497367 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[N:8]=[CH:7][C:6]2[CH:9]=[CH:10][NH:11][C:5]=2[CH:4]=1.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][C:23](=O)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].[OH-].[K+]>CO>[C:13]([O:17][C:18]([N:20]1[CH2:21][CH:22]=[C:23]([C:9]2[C:6]3[CH:7]=[N:8][C:3]([N:2]([CH3:12])[CH3:1])=[CH:4][C:5]=3[NH:11][CH:10]=2)[CH2:24][CH2:25]1)=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 22312002HCID 22312002, compound

Product 1

HCID 69181078HCID 69181078, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dimethyl-(1H-pyrrolo[3,2-c]pyridin-6-yl)-amine (100 mg, 0.62 mmol), 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (248 mg, 1.24 mmol) and potassium hydroxide (139 mg, 2.48 mmol) were added in MeOH (5 mL) and heated to reflux for 16 h. The reaction mixture was then cooled to room temperature and poured into ice water (20 mL). The mixture was extracted with 10% MeOH/CH2Cl2 (5×10 mL). The organic extracts was dried over Na2SO4 and concentrated. The residue was purified by column chromatography (silica, 0-5% MeOH/CH2Cl2) to obtain 180 mg (85%) of the title compound. TLC (silica, 10% MeOH/CH2Cl2): Rf=0.58. MS (electrospray): exact mass calculated for C19H26N4O2, 342.21; m/z found, 343.2 (M++H). 1H NMR (CDCl3, 400 MHz): 9.09 (br s, 1H), 8.76 (s, 1H), 6.90 (d, J=2.15 Hz, 1H), 6.32 (s, 1H), 6.10 (br s, 1H), 4.10-4.05 (m, 2H), 3.62 (t, J=5.87 Hz, 2H), 3.03 (s, 6H), 2.52-2.44 (m, 2H), 1.46 (s, 9H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 16 h
  3. extractionThe mixture was extracted with 10% MeOH/CH2Cl2 (5×10 mL)
  4. dry with materialThe organic extracts was dried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (silica, 0-5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-330b3ff312a4468a9d267b00dff66428
Source dataset
uspto-grants-2005_09
Patent number
US06949540B2

Reaction notes

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