Potassium Hydroxide → HCID 69179929, compound

HRID 586737Notes

Reaction equation

HRID 586737 reaction equation
[N:1]1([C:7]2[N:12]=[CH:11][C:10]3[CH:13]=[CH:14][NH:15][C:9]=3[CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][C:26](=O)[CH2:25][CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17].[OH-].[K+]>CO>[C:16]([O:20][C:21]([N:23]1[CH2:24][CH:25]=[C:26]([C:13]2[C:10]3[CH:11]=[N:12][C:7]([N:1]4[CH2:2][CH2:3][O:4][CH2:5][CH2:6]4)=[CH:8][C:9]=3[NH:15][CH:14]=2)[CH2:27][CH2:28]1)=[O:22])([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 22311994HCID 22311994, compound

Product 1

HCID 69179929HCID 69179929, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-Morpholin-4-yl-1H-pyrrolo[3,2-c]pyridine (197 mg, 0.97 mmol), 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (387 mg, 1.94 mmol) and potassium hydroxide (218 mg, 3.88 mmol) were added in MeOH (10 mL) and heated to reflux for 16 h. The reaction mixture was then cooled to room temperature and poured into ice water (50 mL). The mixture was extracted with 10% MeOH/CH2Cl2 (5×20 mL). The organic extracts was dried over Na2SO4 and concentrated. The residue was purified by column chromatography (silica, 0-5% MeOH/CH2Cl2) to obtain 337 mg (91%) of the desired product. TLC (silica, 5% MeOH/CH2Cl2): Rf=0.50. MS (electrospray): exact mass calculated for C21H28N4O3, 384.22; m/z found, 749.3 [M++H]. 1H NMR (CDCl3, 400 MHz): 9.24 (br s, 1H), 8.77 (s, 1H), 6.95 (d, J=2.15 Hz, 1H), 6.45 (s, 1H), 6.09 (br s, 1H), 4.09-4.04 (m, 2H), 3.66 (t, J=6.06 Hz, 4H), 3.60 (t, J=5.28 Hz, 2H), 3.25 (t, J=5.09 Hz, 4H), 2.38 (d, J=6.26 Hz, 2H), 1.44 (s, 9H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 16 h
  3. extractionThe mixture was extracted with 10% MeOH/CH2Cl2 (5×20 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-ae1d6ca3da8f46cf93f7d19f17e748b6
Source dataset
uspto-grants-2005_08
Patent number
US06936603B2

Reaction notes

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