4-Methoxybenzaldehyde → HCID 11490484, compound

HRID 1727039Notes

Reaction equation

HRID 1727039 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[C:8]2=[N:9][C:10]([N:13]([CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:11][CH:12]=[C:7]2[N:6]=[C:5]1[NH:24][C:25]1[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[C:27]([O:35][CH3:36])[CH:26]=1.[CH:37](=O)[C:38]1[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCl.CO.O>[CH3:45][O:44][C:41]1[CH:42]=[CH:43][C:38]([CH2:37][NH:1][CH2:2][CH2:3][N:4]2[C:8]3=[N:9][C:10]([N:13]([CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:19][CH2:20][CH:21]([CH3:22])[CH3:23])=[CH:11][CH:12]=[C:7]3[N:6]=[C:5]2[NH:24][C:25]2[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[C:27]([O:35][CH3:36])[CH:26]=2)=[CH:39][CH:40]=1

Participants

8

Reactant 4

HCID 312444-MethoxybenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 57566331HCID 57566331, compound

Product 1

HCID 11490484HCID 11490484, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-(2-aminoethyl)-N5,N5-bis(3-methylbutyl)-N2-(3,4,5-trimethoxyphenyl)-3H-imidazo[4,5-b]pyridine-2,5-diamine (83 mg, 1 eq) and p-anisaldehyde (25 mg, 1 eq) in dichloromethane (1.5 ml) is stirred for 6 hours at a temperature of approximately 20° C. The mixture is diluted with methanol (2 ml) then sodium triacetoxyborohydride (70 mg, 2 eq) is added. After stirring for 0.5 hour at a temperature of approximately 20° C., dichloromethane (20 ml) and water saturated with sodium hydrogen carbonate (10 ml) are added to the mixture. After decantation and extractions, the combined organic phases are washed with salt water, dried over Na2SO4 then concentrated under reduced pressure at 40° C. Purification of the residue by flash chromatography on silica gel (eluent: heptane/ethyl acetate 1:1 to 2:8) produces the expected compound (70 mg, 68% yield).

Workup

  1. additionare added to the mixture
  2. extractionAfter decantation and extractions
  3. washthe combined organic phases are washed with salt water
  4. dry with materialdried over Na2SO4
  5. concentrationthen concentrated under reduced pressure at 40° C
  6. customPurification of the residue by flash chromatography on silica gel (eluent: heptane/ethyl acetate 1:1 to 2:8)

Sources & evidence

ORD record
ord-02defa71186e4b1ca94d0a46f10bd066
Source dataset
uspto-grants-2009_02
Patent number
US07495009B2

Reaction notes

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