4-Bromobenzoic acid → HCID 71059874, compound

HRID 2167139Notes

Reaction equation

HRID 2167139 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][CH:27]=1.Cl.[C:36]([O:40][C:41](=[O:45])[CH2:42][CH2:43][NH2:44])([CH3:39])([CH3:38])[CH3:37]>CN(C=O)C>[Br:25][C:26]1[CH:27]=[CH:28][C:29]([C:30]([NH:44][CH2:43][CH2:42][C:41]([O:40][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:45])=[O:32])=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 114644-Bromobenzoic 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 71059874HCID 71059874, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Solid HATU (4.5 g, 11.9 mmol) was added to a DMF solution (5 mL) of 4-bromobenzoic acid (2.0 g, 9.9 mmol), i-Pr2Net (5.3 mL, 14.0 mmol), and β-alanine tert-butyl ester hydrochloride (1.8 g, 9.9 mmol) and the resulting mixture was stirred at room temperature. After 3 days 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 to yield the title compound that was used without further purification.

Workup

  1. concentrationAfter 3 days 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

Sources & evidence

ORD record
ord-bce5cb69b13e41c3bc9087263ecdb87b
Source dataset
uspto-grants-2015_06
Patent number
US09045389B2

Reaction notes

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