Potassium Sodium Tartrate → HCID 118598813, compound

HRID 1050367Notes

Reaction equation

HRID 1050367 reaction equation
[CH3:1][O:2][C:3]1[CH:43]=[CH:42][C:6]([CH2:7][N:8]2C(=O)C3=C(C#N)[CH:13]=[C:14]([N:17]([CH2:24][C:25]4[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=4)[C:18]4[CH:23]=[CH:22][N:21]=[CH:20][N:19]=4)[C:15](=[O:16])[N:10]3[C:9]32[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]3)=[CH:5][CH:4]=1.[H-].C([Al+]CC(C)C)C(C)C.[C@H:54](O)([C:60]([O-:62])=O)[C@@H:55](O)[C:56]([O-:58])=O.[Na+].[K+]>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:56](=[O:58])[C:55]3=[C:54]([CH:60]=[O:62])[CH:13]=[C:14]([N:17]([CH2:24][C:25]4[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=4)[C:18]4[CH:23]=[CH:22][N:21]=[CH:20][N:19]=4)[C:15](=[O:16])[N:10]3[C:9]32[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]3)=[CH:42][CH:43]=1

Participants

5

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 21225700DiisobutylaluminumhydrideHCID 118598665HCID 118598665, compound

Product 1

HCID 118598813HCID 118598813, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2′-(4-methoxybenzyl)-6′-((4-methoxybenzyl)(pyrimidin-4-yl)amino)-1′,5′-dioxo-1′,5′-dihydro-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-a]pyridine]-8′-carbonitrile (3, 1 g, 1.73 mmol) in dichloromethane (20 mL) at 0° C. is added diisobutylaluminum hydride (1 M in dichloromethane, 3.46 mL, 3.46 mmol) dropwise. The reaction is stirred at 0° C. for 2 h. The resulting mixture is poured into saturated aqueous Rochelle's salt solution. The biphasic mixture is stirred overnight and filtered. The filtrate is extracted with dichloromethane. The organic is dried over magnesium sulfate, filtered and concentrated. The crude is purified via column chromatography to afford 2′-(4-methoxybenzyl)-6′-((4-methoxybenzyl)(pyrimidin-4-yl)amino)-1′,5′-dioxo-1′,5′-dihydro-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-a]pyridine]-8′-carbaldehyde (4).

Workup

  1. stirringThe biphasic mixture is stirred overnight
  2. filtrationfiltered
  3. extractionThe filtrate is extracted with dichloromethane
  4. dry with materialThe organic is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude is purified via column chromatography

Sources & evidence

ORD record
ord-774556e784984fa1a58fc39bd8315ad9
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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