Diisobutylaluminum hydride → HCID 58548045, compound

HRID 2207816Notes

Reaction equation

HRID 2207816 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:16][CH2:15][CH:14]([O:17][C:18]2[C:23]([N:24]3[CH2:29][CH2:28][CH:27]([CH:30]=[O:31])[CH2:26][CH2:25]3)=[CH:22][CH:21]=[CH:20][N:19]=2)[CH2:13][CH2:12]1.CC(C[AlH]CC(C)C)C>C1COCC1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:16][CH2:15][CH:14]([O:17][C:18]2[C:23]([N:24]3[CH2:29][CH2:28][CH:27]([CH2:30][OH:31])[CH2:26][CH2:25]3)=[CH:22][CH:21]=[CH:20][N:19]=2)[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 58547973HCID 58547973, compound

Product 1

HCID 58548045HCID 58548045, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(2-((1-(quinolin-2-yl)piperidin-4-yl)oxy)pyridin-3-yl)piperidine-4-carbaldehyde (232 mg, 0.56 mol) in 20 mL of THF was added DIBAL-H (1.4 mol, 1 M in toluene) dropwise at RT. The mixture was stirred for 1 hour at RT and then quenched with saturated aqueous NH4Cl. The resulting mixture was extracted with EtOAc (2×20 mL) and the combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated to give the product (0.150 g, 0.36 mmol, 60% yield). ESI-MS (M+1): 419 calc. for C25H30N4O2 418. 1H NMR (CD3OD, 400 MHz) δ (ppm): 7.96 (d, J=9.2 Hz, 1H); 7.72-7.70 (m, 1H); 7.64-7.60 (m, 2H); 7.52-7.48 (m, 1H); 7.23-7.16 (m, 3H); 6.87-6.84 (m, 1H); 5.38 (s, 1H); 4.81-4.79 (m, 2H); 4.01-3.98 (m, 2H); 3.79-3.74 (m, 2H); 3.40-3.39 (m, 2H); 2.58-2.51 (m, 2H); 2.11-2.08 (m, 2H); 1.93-1.77 (m, 4H); 1.40-1.36 (m, 3H). PDE10 IC50 (uM): 0.01.

Workup

  1. customquenched with saturated aqueous NH4Cl
  2. extractionThe resulting mixture was extracted with EtOAc (2×20 mL)
  3. dry with materialthe combined organic layers were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f70e0ac48baa4cc6bd8dea4c75f8cf7a
Source dataset
uspto-grants-2016_06
Patent number
US09376450B2

Reaction notes

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