Acetic Acid → HCID 68574925, compound

HRID 1949057Notes

Reaction equation

HRID 1949057 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]=[C:14]([NH2:19])[CH:13]=[CH:12]3)[CH:2]=1.[F:20][C:21]1[CH:22]=[CH:23][C:24]([O:29][CH3:30])=[C:25]([CH:28]=1)[CH:26]=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[F:20][C:21]1[CH:22]=[CH:23][C:24]([O:29][CH3:30])=[C:25]([CH:28]=1)[CH2:26][NH:19][C:14]1[CH:13]=[CH:12][C:11]2[C:16](=[CH:17][CH:18]=[C:9]([NH:8][CH2:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[CH:10]=2)[N:15]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 27349435-Fluoro-2-methoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68574335HCID 68574335, compound

Product 1

HCID 68574925HCID 68574925, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

N6-Pyridin-3-ylmethyl-quinoline-2,6-diamine (150 mg, 0.6 mmol) was dissolved in 10 mL dichloromethane. 5-Fluoro-2-methoxybenzaldehyde (111 mg, 0.72 mmol) and acetic acid (72 mg, 1.2 mmol) were added. The reaction mixture was stirred at 40° C. for 3 h. Sodium triacetoxy borohydride (254 mg, 1.2 mmol) was added and stirring was continued at room temperature overnight. The reaction mixture was quenched by addition of 20 mL sat. sodiumbicarbonate solution. The mixture was extracted three times with dichloromethane (20 mL each). The organic phases ware pooled, dried with sodium sulfate, filtered and evaporated. The residue purified by flash chromatography on silica gel (dichloromethane/methanol 100:0->90:10 gradient). The title compound was obtained as a yellow gum (17 mg, 7%), MS: m/e=389.3 (M+H+).

Workup

  1. stirringstirring
  2. waitwas continued at room temperature overnight
  3. customThe reaction mixture was quenched by addition of 20 mL sat. sodiumbicarbonate solution
  4. extractionThe mixture was extracted three times with dichloromethane (20 mL each)
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue purified by flash chromatography on silica gel (dichloromethane/methanol 100:0->90:10 gradient)

Sources & evidence

ORD record
ord-075b628c500f4184a527da444af77b9f
Source dataset
uspto-grants-2013_03
Patent number
US08399674B2

Reaction notes

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