Diisopropylethylamine → HCID 86730052, compound

HRID 1504590Notes

Reaction equation

HRID 1504590 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=[O:13])=[CH:10][N:9]=2)[CH2:4][CH2:3]1.CCN(C(C)C)C(C)C.[C:26](Cl)(=[O:37])[O:27][C:28]1[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=1>N1C=CC=CC=1>[C:26](=[O:37])([O:27][C:28]1[CH:29]=[CH:30][C:31]([N+:34]([O-:36])=[O:35])=[CH:32][CH:33]=1)[O:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12](=[O:13])[NH2:14])=[CH:10][N:9]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 69277538HCID 69277538, compound

Product 1

HCID 86730052HCID 86730052, compoundYield 51.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
30 °C

Procedure

To the solution of 6-(4-hydroxypiperidin-1-yl)nicotinamide (3.32 g, 15 mmol) in pyridine (10 mL) was added DIPEA (3.87 g, 30.0 mmol) and 4-nitrophenyl carbonochloridate (6.03 g, 30 mmol). The resulting mixture was stirred at 30° C. for 2 h before it was concentrated under reduced pressure to afford the crude product. The residue was further purified by silica gel chromatography (DCM: MeOH=100:0 to 20:1) to afford the title compound (3 g, 50%) as a white solid. [LCMS RtB=1.79 min, [M+H]+=387.0].

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customto afford the crude product
  3. customThe residue was further purified by silica gel chromatography (DCM: MeOH=100:0 to 20:1)

Sources & evidence

ORD record
ord-15139e438da844dcbb6dbf30be429731
Source dataset
uspto-grants-2015_12
Patent number
US09216182B2

Reaction notes

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