Acetic Acid → HCID 178463762, compound

HRID 2043359Notes

Reaction equation

HRID 2043359 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]2[N:11]=[CH:12][NH:13][CH:14]=2)=[CH:4][CH:3]=1.[CH:15](=O)[CH3:16].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl>[CH2:15]([N:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[CH2:9][C:10]1[N:11]=[CH:12][NH:13][CH:14]=1)[CH3:16]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 178505872HCID 178505872, compound

Product 1

HCID 178463762HCID 178463762, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of (4-fluoro-phenyl)-(1H-imidazol-4-ylmethyl)-amine (0.20 g, 1.05 mmol) in 1,2-dichloroethane (6 ml) were added acetaldehyde (0.30 ml, 5.23 mmol), sodium triacetoxyborohydride (0.67 g, 3.14 mmol) and acetic acid (0.06 ml). The reaction mixture was stirred at 40° C. for 16 h. The reaction mixture was then concentrated in vacuo and the residue was purified using flash chromatography (column: Isolute® Flash-NH2 (Separtis); eluent: methanol/ethyl acetate/heptane gradient) to yield a white solid (131 mg, 57%); MS (ISP): 220.4 ((M+H)+.).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe residue was purified

Sources & evidence

ORD record
ord-f7ec430c92e643c4bc1bbb1abb9c530b
Source dataset
uspto-grants-2013_11
Patent number
US08586617B2

Reaction notes

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