Acetic Acid → HCID 44219032, compound

HRID 1931512Notes

Reaction equation

HRID 1931512 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([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)[CH:7]=[CH:6]2.[F:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[F:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH:1][CH2:2][C:3]2[CH:4]=[C:5]3[C:10](=[CH:11][CH:12]=2)[N:9]=[C:8]([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)[CH:7]=[CH:6]3)=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 680234-FluorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68628477HCID 68628477, compound

Product 1

HCID 44219032HCID 44219032, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of (6-aminomethyl-quinolin-2-yl)-(R)-indan-1-yl-amine (example 54, step A) (130 mg, 0.45 mmol), 4-fluorobenzaldehyde (61 mg, 0.49 mmol) and acetic acid (108 mg, 1.8 mmol) in 1,2-dichloroethane (5 ml) was stirred at room temperature for 30 min. Afterwards sodium triacetoxy-borohydride (222 mg, 0.94 mmol) was added, the reaction mixture was allowed to stir for 2.5 days at room temperature, poured into ice/saturated sodium bicarbonate solution (30 ml) and extracted with dichloromethane (2×40 ml). The combined organic layers were washed with brine (30 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 a colorless oil (99 mg, 55%). MS: m/e=398.3 (M+H+).

Workup

  1. extractionextracted with dichloromethane (2×40 ml)
  2. washThe combined organic layers were washed with brine (30 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-7fc47502e1784d939d490c07ad9b4c1d
Source dataset
uspto-grants-2012_05
Patent number
US08188284B2

Reaction notes

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