Dipropylamine → Methyl 3-bromo-5-(dipropylcarbamoyl)benzoate

HRID 1454184Notes

Reaction equation

HRID 1454184 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:10]=1)[C:5]([OH:7])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:39]([NH:42][CH2:43][CH2:44][CH3:45])[CH2:40][CH3:41]>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:10]=[C:9]([CH:8]=[C:4]([C:5](=[O:7])[N:42]([CH2:43][CH2:44][CH3:45])[CH2:39][CH2:40][CH3:41])[CH:3]=1)[C:11]([O:13][CH3:14])=[O:12]

Participants

6

Reactant 3

HCID 8902DipropylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 225936413-Bromo-5-(methoxycarbonyl)benzoic acid

Product 1

HCID 21939662Methyl 3-bromo-5-(dipropylcarbamoyl)benzoateYield 99.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-bromo-5-(methoxycarbonyl)benzoic acid (2.0 g, 7.72 mmol) and HATU (3.52 g, 9.27 mmol) in DMF (70 mL) was stirred at room temperature for 10 min. Then dipropylamine (0.78 g, 1.1 mL, 7.72 mmol) was added and the resulting mixture was stirred at room temperature overnight. The mixture was diluted with ethyl acetate, washed with H2O (3 times) and brine, dried over sodium sulfate, and concentrated under vacuum to give the title compound (2.6 g, 99.5% yield): 1H NMR (CD3OD, 500 MHz) δ ppm 0.78 (3H, t, J=5 Hz), 1.01 (3H, t, J=5 Hz), 1.60 (2H, m), 1.74 (2H, m), 3.21 (2H, m), 3.49 (2H, m), 3.96 (3H, s), 7.79 (1H, m), 7.94 (1H, m), 8.23 (1H, m). HPLC retention time: 2.018 min (method B). MS (ESI) (M+H)+ 342.09.

Workup

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. washwashed with H2O (3 times) and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e866cd23467049f5a9ce38a24d43fecc
Source dataset
uspto-grants-2009_01
Patent number
US07476764B2

Reaction notes

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