Tetrahydrofuran → HCID 40211642, compound

HRID 2167140Notes

Reaction equation

HRID 2167140 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1COCC1.[Br:30][C:31]1[CH:39]=[CH:38][C:34]([C:35]([OH:37])=O)=[C:33]([F:40])[CH:32]=1.Cl.[CH3:42][O:43][C:44](=[O:48])[CH2:45][CH2:46][NH2:47]>CCOC(C)=O.Cl>[Br:30][C:31]1[CH:39]=[CH:38][C:34]([C:35]([NH:47][CH2:46][CH2:45][C:44]([O:43][CH3:42])=[O:48])=[O:37])=[C:33]([F:40])[CH:32]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 3026814-Bromo-2-fluorobenzoic acidHCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 40211642HCID 40211642, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

Solid HATU (1.6 g, 4.2 mmol) was added to a THF solution (7 mL) of 4-bromo-2-fluorobenzoic acid (750 mg, 3.2 mmol), i-Pr2Net (1.1 mL, 6.4 mmol), and β-alanine methyl ester hydrochloride (584 mg, 4.2 mmol) and the resulting mixture was stirred at room temperature. After 16 h the resulting mixture was diluted with EtOAc and 1N aqueous HCl. The organic layer was separated, washed with brine, dried (Na2SO4), concentrated, and purified via column chromatography to yield the title compound.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified via column chromatography

Sources & evidence

ORD record
ord-b6e9d210f48842a98b666cffcdd0e43e
Source dataset
uspto-grants-2015_06
Patent number
US09045389B2

Reaction notes

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