Diisopropylethylamine → HCID 178426291, compound

HRID 251147Notes

Reaction equation

HRID 251147 reaction equation
[CH3:1][C:2]1[C:3]([CH2:8][N:9]([CH2:18][C:19]2[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][N:20]=2)[CH:10]2[CH2:15][CH2:14][N:13]([C:16]#[N:17])[CH2:12][CH2:11]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[NH2:26][OH:27].Cl.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH3:1][C:2]1[C:3]([CH2:8][N:9]([CH2:18][C:19]2[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][N:20]=2)[CH:10]2[CH2:15][CH2:14][N:13]([C:16]([NH:26][OH:27])=[NH:17])[CH2:12][CH2:11]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 866238114-[Bis-(3-methyl-pyridin-2-ylmethyl)-amino]-piperidine-1-carbonitrile

Product 1

HCID 178426291HCID 178426291, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-[bis-(3-methyl-pyridin-2-ylmethyl)-amino]-piperidine-1-carbonitrile (0.2413 g, 0.72 mmol) in DMF (7 mL) was added NH2OH.HCl (0.1127 g, 1.44 mmol) and DIPEA (0.25 mL, 1.44 mmol), and stirred at 60° C. for 16 hours. Saturated NaHCO3 (15 mL) was added and extracted with CH2Cl2 (3×50 mL). The combined organic extracts were washed with brine (2×50 mL), dried (Na2SO4), filtered, and concentrated. Purification of the crude material by column chromatography on silica gel (20:1:1 CH2Cl2-MeOH—NH4OH) provided 66.1 mg (58%) of COMPOUND 286 as a yellow solid. 1H NMR (CD3OD) 1.70-1.87 (m, 4H), 2.15 (s, 6H), 2.36-2.58 (m, 3H), 3.71 (d, 2H), 3.82 (s, 4H), 7.19-7.24 (m, 2H), 7.53 (d, 2H, J=7.5 Hz), 8.25 (d, 2H, J=4.8 Hz). 13C NMR (CD3OD) δ 18.70, 28.15, 48.19, 55.78, 59.90, 124.62, 136.04, 140.60, 146.72, 158.48, 160.89. ES-MS m/z 369.3 (M+H). Anal. Calcd. for C20H28N6O.0.9H2O: C, 62.44; H, 7.81; N, 21.85. Found: C, 62.60; H, 7.82; N, 21.74.

Workup

  1. extractionextracted with CH2Cl2 (3×50 mL)
  2. washThe combined organic extracts were washed with brine (2×50 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification of the crude material by column chromatography on silica gel (20:1:1 CH2Cl2-MeOH—NH4OH)

Sources & evidence

ORD record
ord-dfa07c8411c6411abdaefb4d8fd200fe
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

Loading…