Acetic Acid → HCID 25015981, compound

HRID 2076329Notes

Reaction equation

HRID 2076329 reaction equation
[NH2:1][CH2:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7]([NH:13][C@H:14]1[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][CH2:15]1)=[N:8]2.[F:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1.C(O)(=O)C>ClC(Cl)C>[F:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH:1][CH2:2][C:3]2[CH:12]=[CH:11][CH:10]=[C:9]3[C:4]=2[CH:5]=[CH:6][C:7]([NH:13][C@H:14]2[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH2:16][CH2:15]2)=[N:8]3)=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 680234-FluorobenzaldehydeHCID 44219394HCID 44219394, compound

Product 1

HCID 25015981HCID 25015981, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of (5-aminomethyl-quinolin-2-yl)-(R)-indan-1-yl-amine (example 80, step B) (200 mg, 0.69 mmol), 4-fluorobenzaldehyde (94 mg, 0.76 mmol) and acetic acid (166 mg, 2.76 mmol) in 1,1-dichloroethane (10 ml) was stirred at room temperature for 30 minutes. Afterwards sodium triacetoxy-boron hydride (342 mg, 1.61 mmol) was added, the reaction mixture was allowed to stir for 17 hours at room temperature, poured into ice/saturated NaHCO3 solution (20 ml) and extracted with ethyl acetate (3×50 ml). The combined organic layers were washed with brine (50 ml), dried (MgSO4) and evaporated. The crude product was purified by flash chromatography (ethyl acetate/heptane) on silica gel to yield the title compound as light yellow oil (130 mg, 47%).

Workup

  1. extractionextracted with ethyl acetate (3×50 ml)
  2. washThe combined organic layers were washed with brine (50 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe crude product was purified by flash chromatography (ethyl acetate/heptane) on silica gel

Sources & evidence

ORD record
ord-d3553af8b60249078e25b5e7369891aa
Source dataset
uspto-grants-2011_04
Patent number
US07923561B2

Reaction notes

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