Diethylamine → HCID 16035625, compound

HRID 2220484Notes

Reaction equation

HRID 2220484 reaction equation
[NH2:1][C:2]1[N:3]([CH3:31])[C:4](=[O:30])[C:5]([C:20]2[CH:21]=[C:22]([CH:28]=O)[N:23]([CH2:25][CH2:26][F:27])[CH:24]=2)([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]3[C:14]([F:19])=[N:15][CH:16]=[CH:17][CH:18]=3)[CH:8]=2)[N:6]=1.[CH2:32]([NH:34][CH2:35][CH3:36])[CH3:33].[BH3-]C#N.[Na+]>[Cl-].[Cl-].[Zn+2].CO>[NH2:1][C:2]1[N:3]([CH3:31])[C:4](=[O:30])[C:5]([C:20]2[CH:21]=[C:22]([CH2:28][N:34]([CH2:35][CH3:36])[CH2:32][CH3:33])[N:23]([CH2:25][CH2:26][F:27])[CH:24]=2)([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]3[C:14]([F:19])=[N:15][CH:16]=[CH:17][CH:18]=3)[CH:8]=2)[N:6]=1

Participants

6

Reactant 3

HCID 8021DiethylamineHCID 5003444Sodium cyanoborohydrideHCID 15949657HCID 15949657, compound

Product 1

HCID 16035625HCID 16035625, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Procedure

To a glass tube was added methanol (0.5 mL), 4-{2-amino-4-[3-(2-fluoropyridin-3-yl)phenyl]-1-methyl-5-oxo-4,5-dihydro-1H-imidazol-4-yl}-1-(2-fluoroethyl)-1H-pyrrole-2-carbaldehyde (0.05 g; 0.12 mmol), diethylamine (43 μL; 0.41 mmol), and 1.8 mL of a methanolic solution of ZnCl2 (0.1 M), and NaBH3CN (0.2 M). The mixture was stirred 24 hours at room temperature. The solvent was evaporated and the residue was dissolved in chloroform, washed with 0.1 N NaOH solution, dried over MgSO4, and evaporated to give the title compound as an amorphous white solid, 0.021 g (37% yield), mp 121-140° C.; MS (ES) m/z 479.2, [M−H]−.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in chloroform
  3. washwashed with 0.1 N NaOH solution
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-84fdafdf80b54d66bf69adc02d49a1b6
Source dataset
uspto-grants-2008_08
Patent number
US07417047B2

Reaction notes

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