Acetic Acid → (5-Methyl-furan-2-ylmethyl)-[5-(pyridin-3-ylaminomethyl)-quinolin-2-yl]-amine

HRID 1170089Notes

Reaction equation

HRID 1170089 reaction equation
[CH3:1][C:2]1[O:6][C:5]([CH2:7][NH:8][C:9]2[CH:18]=[CH:17][C:16]3[C:15]([CH:19]=O)=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=2)=[CH:4][CH:3]=1.[NH2:21][C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)CCl>[CH3:1][C:2]1[O:6][C:5]([CH2:7][NH:8][C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[CH2:19][NH:21][C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)[N:10]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 100093-AminopyridineHCID 5049666Sodium triacetoxyborohydrideHCID 866194932-[(5-Methyl-furan-2-ylmethyl)-amino]-quinoline-5-carbaldehyde

Product 1

HCID 68434149(5-Methyl-furan-2-ylmethyl)-[5-(pyridin-3-ylaminomethyl)-quinolin-2-yl]-amine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

2-[(5-Methyl-furan-2-ylmethyl)-amino]-quinoline-5-carbaldehyde (100 mg, 0.376 mmol) was dissolved in 5 mL ethylendichloride. 3-Aminopyridine (50 mg, 0.532 mmol) and acetic acid (90 mg, 1.50 mmol) were added. The reaction mixture was stirred at room temperature for 1 h. Sodium triacetoxy borohydride (172 mg, 0.811 mmol) was added and stirring was continued overnight. The reaction mixture was quenched by addition of 50 mL water. The mixture was extracted three times with dichloromethane (50 mL each). The organic phases ware pooled, dried with sodium sulfate, filtered and evaporated. The crude product was recrystallized from dichloromethane. The title compound was obtained as a white solid (50 mg, 39%), MS: m/e=345.0 (M+H+).

Workup

  1. stirringstirring
  2. waitwas continued overnight
  3. customThe reaction mixture was quenched by addition of 50 mL water
  4. extractionThe mixture was extracted three times with dichloromethane (50 mL each)
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product was recrystallized from dichloromethane

Sources & evidence

ORD record
ord-b5d78e0a348141ceb3641c73234287c0
Source dataset
uspto-grants-2010_11
Patent number
US07825253B2

Reaction notes

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