Triethylamine → HCID 59829681, compound

HRID 551138Notes

Reaction equation

HRID 551138 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:32](Cl)(=[O:36])[CH:33]([CH3:35])[CH3:34].C(N(CC)CC)C>O1CCCC1>[CH2:1]([O:8][C:9]1[C:10]([CH2:20][CH:21]([NH:22][C:32](=[O:36])[CH:33]([CH3:35])[CH3:34])[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 62325Isobutyryl chlorideHCID 59829670HCID 59829670, compound

Product 1

HCID 59829681HCID 59829681, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a round bottom flask containing 2-[8-(benzyloxy)-5-chloroquinolin-7-yl]-1-{5-[(dimethylamino)methyl]-2-furyl}ethanamine (0.710 mmol) at 0° C. was added a solution of isobutyryl chloride (0.852 mmol, 1.2 eq.) and triethylamine (0.852 mmol, 1.2 eq.) in tetrahydrofuran (5 mL) that was pre-mixed and stirred 5 min prior to addition. After warming to room temperature, the resulting solution was stirred 2 h and quenched with saturated aqueous sodium bicarbonate solution (1 mL) and stirred 5 min. The reaction was diluted with 0.1N NaOH (15 mL) and extracted with ethyl acetate (3×10 mL). The combined organic layers were dried (MgSO4), filtered and concentrated to a yellow syrup that was purified by column chromatography to afford the final product as a white solid (0.344 mmol, 47% for 2 steps). HRMS: calcd for C29H32ClN3O3+H+, 506.22049; found (ESI, [M+H]+ Obs'd), 506.2208.

Workup

  1. additionwas pre-mixed
  2. additionto addition
  3. stirringthe resulting solution was stirred 2 h
  4. customquenched with saturated aqueous sodium bicarbonate solution (1 mL)
  5. stirringstirred 5 min
  6. additionThe reaction was diluted with 0.1N NaOH (15 mL)
  7. extractionextracted with ethyl acetate (3×10 mL)
  8. dry with materialThe combined organic layers were dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated to a yellow syrup that
  11. customwas purified by column chromatography

Sources & evidence

ORD record
ord-9207b990eff14c3287a9061dd2653b7e
Source dataset
uspto-grants-2011_05
Patent number
US07947712B2

Reaction notes

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