HCID 86669822, compound → HCID 68182226, compound

HRID 1620237Notes

Reaction equation

HRID 1620237 reaction equation
[CH:1]([C:3]1[C:4]([NH:15][CH2:16][CH2:17][NH:18][C:19](=[O:21])[CH3:20])=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:13][CH3:14])=[CH:8][CH:7]=2)=[O:2]>C1COCC1>[OH:2][CH2:1][C:3]1[C:4]([NH:15][CH2:16][CH2:17][NH:18][C:19](=[O:21])[CH3:20])=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:13][CH3:14])=[CH:8][CH:7]=2

Participants

3

Reactant 1

HCID 86669822HCID 86669822, compound2×

Product 1

HCID 68182226HCID 68182226, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of N-(2-((3-formyl-6-methoxyquinolin-2-yl)amino)ethyl)acetamide SLA 41086 (147 mg, 512 μmol) in THF (20 mL) in a 100 mL round-bottomed flask equipped with a magnetic stirrer was added sodium borohydride NaBH4 (19 mg, 502 μmol) and the mixture was stirred overnight at RT then cooled in an ice bath before quenching by addition of a 1 N aq. HCl solution (40 mL). After stirring for 15 min at that temperature, the mixture was basified to pH=9 with a 2 N aq. NaOH solution. THF was then removed at 40° C. under vacuum and the solution was extracted with CH2Cl2 (100 mL). The organic layer was washed with brine (20 mL), dried over Na2SO4, filtered and concentrated under vacuum to give N-(2-((3-(hydroxymethyl)-6-methoxyquinolin-2-yl)amino)ethyl)acetamide SLA 41088 as an orange solid (113 mg, 76% yield).

Workup

  1. temperaturethen cooled in an ice bath
  2. custombefore quenching by addition of a 1 N aq. HCl solution (40 mL)
  3. stirringAfter stirring for 15 min at that temperature
  4. customTHF was then removed at 40° C. under vacuum
  5. extractionthe solution was extracted with CH2Cl2 (100 mL)
  6. washThe organic layer was washed with brine (20 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ec9271995f2d4a71bbc6afc5f3313115
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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