Pyrrolidine → HCID 86732799, compound

HRID 525930Notes

Reaction equation

HRID 525930 reaction equation
[Cl:1][C:2]1[C:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[C:10]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:36])[C:5]([CH:34]=O)=[N:6][N:7]2[CH2:32][CH3:33].[NH:37]1[CH2:41][CH2:40][CH2:39][CH2:38]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Cl:1][C:2]1[C:11]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)=[C:10]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:36])[C:5]([CH2:34][N:37]1[CH2:41][CH2:40][CH2:39][CH2:38]1)=[N:6][N:7]2[CH2:32][CH3:33]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 86732797HCID 86732797, compound

Product 1

HCID 86732799HCID 86732799, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-chloro-1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydrocinnoline-3-carbaldehyde (3.5 g, 4.26 mmol) in Dichloromethane (DCM) (80 mL) was added pyrrolidine (0.370 mL, 4.48 mmol) and sodium triacetoxyborohydride (1.355 g, 6.40 mmol). The mixture was stirred at r.t. for 1 h. Then reaction mixture was washed with sat. NaHCO3 (aq.) and brine, dried over sodium sulfate and the solvent was removed in vacuo. The crude product was then purified through normal phase chromatography (CombiFlash Rf), eluting with MeOH/DCM (0-20%) to afford 5-chloro-1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-3-(pyrrolidin-1-ylmethyl)cinnolin-4(1H)-one (1.9 g, 3.37 mmol, 79% yield) as an orange solid. The desired product was dissolved in DCM and washed with sat. NaHCO3 (aq.) and brine, concentrated and passed through a flash column chromatography before being used for the next step. LCMS: (M+H)+: 564.4.

Workup

  1. customThen reaction mixture
  2. washwas washed with sat. NaHCO3 (aq.) and brine
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was removed in vacuo
  5. customThe crude product was then purified through normal phase chromatography (CombiFlash Rf)
  6. washeluting with MeOH/DCM (0-20%)

Sources & evidence

ORD record
ord-211da4d124364e628f949967b7c3de93
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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