Acetaldehyde → HCID 22485158, compound

HRID 1368264Notes

Reaction equation

HRID 1368264 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 A 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-f0598c18388d473ab0f903c20456aa02
Source dataset
uspto-grants-2003_06
Patent number
US06573274B1

Reaction notes

Loading…