Acetaldehyde → HCID 22485158, compound

HRID 2181056Notes

Reaction equation

HRID 2181056 reaction equation
[Cl:1][C:2]1[CH:29]=[C:28]([NH:30][CH3:31])[CH:27]=[CH:26][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([C:14](=[O:24])[NH:15][S:16]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])(=[O:18])=[O:17])=[CH:12][CH:13]=[C:8]2[N:7]=[C:6]1[CH3:25].CO.[CH:34](=O)[CH3:35].C([BH3-])#N.[Na+]>O1CCCC1.C(Cl)(Cl)Cl.CO.C(O)(=O)C>[Cl:1][C:2]1[CH:29]=[C:28]([N:30]([CH2:34][CH3:35])[CH3:31])[CH:27]=[CH:26][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([C:14](=[O:24])[NH:15][S:16]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])(=[O:18])=[O:17])=[CH:12][CH:13]=[C:8]2[N:7]=[C:6]1[CH3:25]

Participants

8

Reactant 4

HCID 177Acetaldehyde2×HCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 22485111HCID 22485111, compound

Product 1

HCID 22485158HCID 22485158, compoundYield 80.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolventHCID 21584188Chloroform methanolSolvent

Procedure

To a suspension of 3-(2-chloro-4-(methylamino)benzyl)-2-methyl-5-(1-pentanesulfonylcarbamoyl)-3H-imidazo[4,5-b]pyridine (232 mg) in tetrahydrofuran (1.2 ml)-methanol (1.2 ml) were added acetaldehyde (106 mg), sodium cyanoborohydride (65 mg) and acetic acid (60 mg) at room temperature, and the mixture was stirred. After 2 hr, acetaldehyde (80 mg) was added and the mixture was stirred for 2 hr. The reaction mixture was diluted with chloroform/methanol (10/1)(10 ml), washed successively with water, 1N hydrochloric acid and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was recrystallized from acetone-water to give 3-(2-chloro-4-(ethylmethylamino)benzyl)-2-methyl-5-(1-pentanesulfonylcarbamoyl)-3H-imidazo[4,5-b]pyridine (197 mg) as a white powder.

Workup

  1. stirringthe mixture was stirred for 2 hr
  2. washwashed successively with water, 1N hydrochloric acid and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was recrystallized from acetone-water

Sources & evidence

ORD record
ord-ddbbc95781e34abe972690c67c3dcf46
Source dataset
uspto-grants-2005_05
Patent number
US06890934B2

Reaction notes

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