Triethylamine → HCID 59829687, compound

HRID 551137Notes

Reaction equation

HRID 551137 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH2:20][CH:21]([C:23]2[O:24][C:25]([CH2:28][N:29]([CH3:31])[CH3:30])=[CH:26][CH:27]=2)[NH2:22])=[CH:11][C:12]([Cl:19])=[C:13]2[C:18]=1[N:17]=[CH:16][CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[O:39]([CH2:46][C:47](Cl)=[O:48])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>O1CCCC1>[CH2:1]([O:8][C:9]1[C:10]([CH2:20][CH:21]([NH:22][C:47](=[O:48])[CH2:46][O:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:23]2[O:24][C:25]([CH2:28][N:29]([CH3:30])[CH3:31])=[CH:26][CH:27]=2)=[CH:11][C:12]([Cl:19])=[C:13]2[C:18]=1[N:17]=[CH:16][CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69703Phenoxyacetyl chlorideHCID 59829670HCID 59829670, compound

Product 1

HCID 59829687HCID 59829687, compoundYield 26.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirring solution of 2-[8-(benzyloxy)-5-chloroquinolin-7-yl]-1-{5-[(dimethylamino)methyl]-2-furyl}ethanamine (0.431 mmol) and triethylamine (0.474 mmol, 1.1 eq.) in tetrahydrofuran (4 mL) at 0° C. was added phenoxyacetyl chloride (0.474 mmol, 1.1 eq.) and the resulting solution was stirred 5 min at 0° C. then warmed to room temperature and stirred 15 min. The reaction was quenched with saturated aqueous sodium bicarbonate solution (15 mL) and the resulting aqueous solution was extracted with ethyl acetate (3×10 mL). The combined organic layers were dried (MgSO4), filtered and concentrated to a white foam that was purified by column chromatography using 10% methanol/dichloromethane to give the final product as a clear oil (0.113 mmol, 26%). MS (ESI) m/z 570.3; HRMS: calcd for C33H32ClN3O4+H+, 570.21541; found (ESI, [M+H]+ Obs'd), 570.2155.

Workup

  1. temperaturethen warmed to room temperature
  2. stirringstirred 15 min
  3. customThe reaction was quenched with saturated aqueous sodium bicarbonate solution (15 mL)
  4. extractionthe resulting aqueous solution was extracted with ethyl acetate (3×10 mL)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated to a white foam that
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-aa297bed209a48ccb5e9bb645d2890ad
Source dataset
uspto-grants-2011_05
Patent number
US07947712B2

Reaction notes

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