Citric Acid → HCID 68575249, compound

HRID 2111902Notes

Reaction equation

HRID 2111902 reaction equation
C(N(CC)CC)C.[CH3:8][N:9]1[C:13]([C:14](Cl)=[O:15])=[CH:12][C:11]([CH3:17])=[N:10]1.[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][CH:28]([NH:31][CH2:32][CH:33]([CH3:35])[CH3:34])[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(OCC)C>[C:18]([O:22][C:23]([N:25]1[CH2:26][CH2:27][CH:28]([N:31]([C:14]([C:13]2[N:9]([CH3:8])[N:10]=[C:11]([CH3:17])[CH:12]=2)=[O:15])[CH2:32][CH:33]([CH3:35])[CH3:34])[CH2:29][CH2:30]1)=[O:24])([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8471TriethylamineHCID 27362992,5-Dimethyl-2H-pyrazole-3-carbonyl chlorideHCID 15380699tert-Butyl 4-(isobutylamino)piperidine-1-carboxylate

Product 1

HCID 68575249HCID 68575249, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Triethylamine (1.8 ml, 12.8 mmol) and 1,3-dimethyl-1H-pyrazole-5-carbonyl chloride (0.5 g, 3.2 mmol) is added to a stirred solution of 4-isobutylamino-piperidine-1-carboxylic acid tert-butyl ester (0.82 g, 3.2 mmol), and diethyl ether (30 ml). The reaction is stirred for 5 minutes at room temperature. The reaction is poured into 5% citric acid and extracted with ethyl acetate. The ethyl acetate is washed with sodium bicarbonate and brine and dried over sodium sulfate. The sodium sulfate is filtered off and the crude product is concentrated on a rotary evaporator to yield (1.15 g, 96% crude) of 4-{[(1,3-dimethyl-1H-pyrazol-5-yl)-carbonyl]-isobutyl-amino}-piperidine-1-carboxylic acid tert-butyl ester: mass spectrum (ion spray): m/z=379 (M++1); 1H NMR (CD3OD) (broad peaks due to rotamers) δ=6.29-6.17 (1H, br m), 4.23-4.10 (2H, br m), 3.98-3.90 (1H, br m), 3.78 (3H, br s), 3.25 (2H, d), 2.89-2.57 (2H, br m), 2.25 (3H, s), 2.20-2.04 (1H, br m), 1.86-1.70 (3H, br m), 1.46 (9H, s), 1.00-0.74 (6H, br m).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate is washed with sodium bicarbonate and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationThe sodium sulfate is filtered off
  5. concentrationthe crude product is concentrated on a rotary evaporator

Sources & evidence

ORD record
ord-8c70763abfdb49bb9aac4d7e7a9c178c
Source dataset
uspto-grants-2009_04
Patent number
US07521462B2

Reaction notes

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