Dimethylamine → 1-(4-(7-Chlorothieno[3,2-b]pyridin-2-yl)-1-ethyl-1H-imidazol-2-yl)-N,N-dimethylmethanamine

HRID 418633Notes

Reaction equation

HRID 418633 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[N:12]=[C:13]([CH:18]=O)[N:14]([CH2:16][CH3:17])[CH:15]=3)[S:10][C:3]=12.[CH3:20][NH:21][CH3:22].C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[N:12]=[C:13]([CH2:18][N:21]([CH3:22])[CH3:20])[N:14]([CH2:16][CH3:17])[CH:15]=3)[S:10][C:3]=12

Participants

6

Reactant 3

HCID 674DimethylamineHCID 5003444Sodium cyanoborohydrideHCID 587902554-(7-Chlorothieno[3,2-b]pyridin-2-yl)-1-ethyl-1H-imidazole-2-carbaldehyde

Product 1

HCID 587902451-(4-(7-Chlorothieno[3,2-b]pyridin-2-yl)-1-ethyl-1H-imidazol-2-yl)-N,N-dimethylmethanamineYield 34.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of the aldehyde 111 (344 mg, 1.18 mmol) and dimethylamine (0.7 mL, 1.41 mmol) in methanol (24 mL) and acetic acid (few drops) were stirred at RT overnight. Sodium cyanoborohydride (237 mg, 3.77 mmol) was added and the reaction mixture was allowed to stir at room temperature until completion of the reaction. The solvents were evaporated and water was added to the residue and the mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and evaporated. The crude product was purified by flash chromatography (eluent: 2.5% MeOH/97.5% DCM to 10% MeOH/90% DCM) to afford title compound 112 as a yellow solid (129 mg, 34% yield). MS (m/z): 321.1 (M+H).

Workup

  1. stirringto stir at room temperature until completion of the reaction
  2. customThe solvents were evaporated
  3. additionwater was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude product was purified by flash chromatography (eluent: 2.5% MeOH/97.5% DCM to 10% MeOH/90% DCM)

Sources & evidence

ORD record
ord-d5534eb7c5f54016bc90194aebf254e9
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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