Acetic Acid → HCID 10365615, compound

HRID 1791339Notes

Reaction equation

HRID 1791339 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:29][CH3:30])=[C:6]([C:8]([CH3:28])([CH3:27])[CH2:9][C:10]([NH2:26])([CH2:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=[CH:18][CH:17]=2)[C:11]([F:14])([F:13])[F:12])[CH:7]=1.C=O.[C:33](O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:29][CH3:30])=[C:6]([C:8]([CH3:27])([CH3:28])[CH2:9][C:10]([NH:26][CH3:33])([CH2:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=[CH:18][CH:17]=2)[C:11]([F:12])([F:14])[F:13])[CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 10319953HCID 10319953, compound

Product 1

HCID 10365615HCID 10365615, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 3-(5-fluoro-2-methoxy-phenyl)-3-methyl-1-quinolin-4-ylmethyl-1-trifluoromethyl-butylamine (42.0 mg, 0.1 mmol) and formaldehyde (8 μL, 0.1 mmol) in dichloroethane (2 mL) was stirred for 30 min at room temperature in the presence of 4A molecular sieves (200 mg). The reaction mixture was acidified with acetic acid (57 μL, 1.0 mmol), stirred for 16 h and treated with sodium triacetoxy borohydride (42.4 mg, 0.2 mmol). The resulting mixture was stirred at room temperature for 3 h and quenched with NaHCO3 (sat. 6 mL). Phases were separated and the aqueous layer was extracted with CHCl3 (2×4 mL). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. The residue was purified on SiO2 (20%–40%, EtOAc:Hexanes) to give 24.0 mg (55%) of the title compound.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 3 h
  2. customquenched with NaHCO3 (sat. 6 mL)
  3. customPhases were separated
  4. extractionthe aqueous layer was extracted with CHCl3 (2×4 mL)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified on SiO2 (20%–40%, EtOAc:Hexanes)

Sources & evidence

ORD record
ord-78f61fc663da4dc2a337552f1b74b830
Source dataset
uspto-grants-2006_07
Patent number
US07074806B2

Reaction notes

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