Pyrrolidine → HCID 86732740, compound

HRID 525873Notes

Reaction equation

HRID 525873 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=3)=[C:15]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[CH:16]=2)[C:11](=[O:38])[C:10]([CH:39]=O)=[N:9]1)[CH3:7].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(O)(=O)C>[CH2:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([O:28][CH2:29][C:30]3[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=3)=[C:15]([O:18][CH2:19][C:20]3[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=3)[CH:16]=2)[C:11](=[O:38])[C:10]([CH2:39][N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[N:9]1)[CH3:7]

Participants

6

Reactant 3

HCID 31268PyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 86732739HCID 86732739, compound

Product 1

HCID 86732740HCID 86732740, compoundYield 77.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolvent

Procedure

A solution of pyrrolidine (0.167 mL, 2.017 mmol) and 1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydrocinnoline-3-carbaldehyde (0.87 g, 1.833 mmol) in 1,2-dichloroethane (DCE) (19 mL) and 2 drops of acetic acid was treated with sodium triacetoxyborohydride (0.583 g, 2.75 mmol). The reaction mixture was stirred for 1.5 h and then concentrated. The residue was purified by automatic silica gel column chromatography (Combiflash RF), eluting with [dichloromethane/methanol/ammonium hydroxide (80:20:2)]/dichloromethane (0-60%) to afford 1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-3-(pyrrolidin-1-ylmethyl)cinnolin-4(1H)-one (750 mg, 1.416 mmol, 77% yield) as a light yellow gummy solid. LCMS: (M+H)+: 530.3

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by automatic silica gel column chromatography (Combiflash RF)
  3. washeluting with [dichloromethane/methanol/ammonium hydroxide (80:20:2)]/dichloromethane (0-60%)

Sources & evidence

ORD record
ord-582cb834103e4d8e85963f1ae0ca97be
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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