Triethylamine → HCID 86732738, compound

HRID 525871Notes

Reaction equation

HRID 525871 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)=[C:10]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[CH:11]=2)[C:6](=[O:33])[C:5]([C:34](O)=[O:35])=[N:4]1)[CH3:2].C(N(CC)CC)C.ClC(OCC)=O.[BH4-].[Na+]>O1CCCC1.C(O)C>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([O:23][CH2:24][C:25]3[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=3)=[C:10]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[CH:11]=2)[C:6](=[O:33])[C:5]([CH2:34][OH:35])=[N:4]1)[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 86732737HCID 86732737, compound

Product 1

HCID 86732738HCID 86732738, compoundYield 79.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydrocinnoline-3-carboxylic acid (2.25 g, 4.59 mmol) in tetrahydrofuran (THF) (60 mL) was added triethylamine (2.110 mL, 15.14 mmol) and ethyl chloroformate (1.322 mL. 13.76 mmol). The resulting yellow solution was stirred at room temperature for 2 h, and was then added to a solution of sodium borohydride (2.083 g, 55.0 mmol) in ethanol (60 mL). After being stirred for 2 h, the reaction was quenched by addition of water (5 mL). The organic solvent was removed in vacuo, the residue was then taken in water (50 mL) and extracted with dichloromethane (2×50 mL). The combined extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by automatic silica gel column chromatography (Combiflash RF), eluting with methanol/dichloromethane (0-10%) to afford 1-ethyl-3-(hydroxymethyl)-6,7-bis((4-methoxybenzyl)oxy)cinnolin-4(1H)-one (1.97 g, 3.64 mmol, 79% yield) as a white solid. LCMS: (M+H)+: 477.1

Workup

  1. stirringAfter being stirred for 2 h
  2. customthe reaction was quenched by addition of water (5 mL)
  3. customThe organic solvent was removed in vacuo
  4. extractionextracted with dichloromethane (2×50 mL)
  5. dry with materialThe combined extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by automatic silica gel column chromatography (Combiflash RF)
  9. washeluting with methanol/dichloromethane (0-10%)

Sources & evidence

ORD record
ord-2162617e882c49ca9ace791f56b9b51c
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

Loading…