tert-Butyl bromoacetate → HCID 59463645, compound

HRID 1713131Notes

Reaction equation

HRID 1713131 reaction equation
[CH:1]1([NH:5][C:6]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[N:13][CH:14]=3)[N:9]=2)=[O:7])[CH2:4][CH2:3][CH2:2]1.Br[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].[BH4-].[Na+]>CC#N>[CH:1]1([NH:5][C:6]([C:8]2[CH:17]=[CH:16][C:15]3[CH2:14][N:13]([CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:12][CH2:11][C:10]=3[N:9]=2)=[O:7])[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 79177tert-Butyl bromoacetateHCID 4311764Sodium borohydrideHCID 57420578N-cyclobutyl-1,6-naphthyridine-2-carboxamide

Product 1

HCID 59463645HCID 59463645, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of N-cyclobutyl-1,6-naphthyridine-2-carboxamide (227 mg, 1 mmol), tert-butyl bromoacetate (234 mg, 1.2 mmol) in CH3CN (15 mL) is refluxed overnight. Solvent is removed in vacuo and the residue is dissolve in MeOH (20 mL). To the solution is added NaBH4 (181 mg, 4.8 mmol) and the mixture is refluxed for 4 hr. The solvent is removed in vacuo and the residue is partitioned between water (20 mL) and EtOAc (20 mL). The layers are separated and the aqueous layer is extracted with EtOAc (20 ml). The combined extracts are washed with brine (10 mL), dried and evaporated. The residue is purified by flash column to give the title compound as a light yellow oil. MS (M+1): 346.2.

Workup

  1. temperatureis refluxed overnight
  2. customSolvent is removed in vacuo
  3. dissolutionthe residue is dissolve in MeOH (20 mL)
  4. temperaturethe mixture is refluxed for 4 hr
  5. customThe solvent is removed in vacuo
  6. customthe residue is partitioned between water (20 mL) and EtOAc (20 mL)
  7. customThe layers are separated
  8. extractionthe aqueous layer is extracted with EtOAc (20 ml)
  9. washThe combined extracts are washed with brine (10 mL)
  10. customdried
  11. customevaporated
  12. customThe residue is purified by flash column

Sources & evidence

ORD record
ord-f61137e8a4cc441abd933f7f71054eb7
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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