4-Bromo-3-methylbenzoic acid → HCID 71059814, compound

HRID 2167138Notes

Reaction equation

HRID 2167138 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Br:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([OH:32])=O)=[CH:28][C:27]=1[CH3:35].Cl.[C:37]([O:41][C:42](=[O:46])[CH2:43][CH2:44][NH2:45])([CH3:40])([CH3:39])[CH3:38]>CN(C=O)C>[Br:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([NH:45][CH2:44][CH2:43][C:42]([O:41][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:46])=[O:32])=[CH:28][C:27]=1[CH3:35]

Participants

5

Reactant 3

HCID 821314-Bromo-3-methylbenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 16218890Tert-butyl 3-aminopropanoate hydrochloride

Product 1

HCID 71059814HCID 71059814, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Solid HATU (2.1 g, 5.6 mmol) was added to a DMF solution (25 mL) of 4-bromo-3-methylbenzoic acid (1.0 g, 4.7 mmol), i-Pr2Net (2.4 mL, 14.0 mmol), and β-alanine tert-butyl ester hydrochloride (845 mg, 4.7 mmol) and the resulting mixture was stirred at room temperature. After 16 h the resulting mixture was concentrated, diluted with EtOAc, washed with water, 1N KHSO4, water, saturated aqueous NaHCO3, and brine. The organic layer was dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.

Workup

  1. concentrationAfter 16 h the resulting mixture was concentrated
  2. additiondiluted with EtOAc
  3. washwashed with water, 1N KHSO4, water, saturated aqueous NaHCO3, and brine
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified via column chromatography

Sources & evidence

ORD record
ord-df3b01b02aee4876809a06bcfee33dc8
Source dataset
uspto-grants-2015_06
Patent number
US09045389B2

Reaction notes

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