Benzaldehyde → HCID 67411902, compound

HRID 2035548Notes

Reaction equation

HRID 2035548 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]([N:13]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[C:14]2[CH:15]=[N:16][C:17]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[CH:18][CH:19]=2)=[CH:10][C:11]=1[NH2:12])=[O:5])[CH3:2].[CH:35](=O)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C([Sn](Cl)(Cl)CCCC)CCC.C1([SiH3])C=CC=CC=1>O1CCCC1.O>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]([N:13]([CH2:26][C:27]2[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=2)[C:14]2[CH:15]=[N:16][C:17]([N:20]3[CH2:21][CH2:22][O:23][CH2:24][CH2:25]3)=[CH:18][CH:19]=2)=[CH:10][C:11]=1[NH:12][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 240Benzaldehyde2×HCID 12688Dibutyltin dichloride2×HCID 12752Phenylsilane2×HCID 67412646HCID 67412646, compound

Product 1

HCID 67411902HCID 67411902, compoundYield 5.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

47 mg of 4-amino-6-[4-methoxybenzyl-(6-morpholinopyridin-3-yl)amino]pyridine-3-carboxylic acid ethyl ester was dissolved in 2 mL of tetrahydrofuran, to which 21.5 mg of benzaldehyde, 3.1 mg of dibutyltin dichloride and 16.4 mg of phenylsilane were added, and stirred at room temperature for 3 days. For every 24 hours in the meantime, 21.5 mg of benzaldehyde, 3.1 mg of dibutyltin dichloride and 16.4 mg of phenylsilane were each added twice. To the reaction mixture water was added, extracted with chloroform, the extract was washed with saturated saline, and dried on anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel thin layer chromatography (hexane:ethyl acetate=1:1) and silica gel thin layer chromatography (chloroform:methanol=20:1) to obtain 3.0 mg of the title compound crude product containing impurities as a light yellow oil. Without further purification, this was used in the next reaction as it was.

Workup

  1. additionwere added
  2. additioneach added twice
  3. extractionextracted with chloroform
  4. washthe extract was washed with saturated saline
  5. dry with materialdried on anhydrous sodium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was purified by silica gel thin layer chromatography (hexane:ethyl acetate=1:1) and silica gel thin layer chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-4d83737e2bbd453a91bb3131d613fb13
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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