Sodium borohydride → HCID 68182226, compound

HRID 1620267Notes

Reaction equation

HRID 1620267 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].[BH4-].[Na+]>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

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86669822HCID 86669822, compound2×

Product 1

HCID 68182226HCID 68182226, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of N-(2-(3-formyl-6-methoxyquinolin-2-ylamino)ethyl)acetamide SLA 41168 (0.70 g, 2.43 mmol) in THF (30 mL) in a 100 mL round-bottomed flask equipped with a magnetic stirrer was added NaBH4 (0.09 g, 2.43 mmol) 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, the mixture was basified to pH=9 using a 2 N aq. NaOH solution. THF was removed at 40° C. under vacuum and the solution was extracted with CH2Cl2 (200 mL), washed with brine (20 mL), dried over Na2SO4, filtered and concentrated to give N-(2-(3-(hydroxymethyl)-6-methoxyquinolin-2-ylamino)ethyl)acetamide SLA 41174 as an orange solid (0.65 g, 93% 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
  4. customTHF was removed at 40° C. under vacuum
  5. extractionthe solution was extracted with CH2Cl2 (200 mL)
  6. washwashed with brine (20 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-66ca96972ee446f8a849bd260987cecc
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

Loading…