Methanol → HCID 82547484, compound

HRID 1056362Notes

Reaction equation

HRID 1056362 reaction equation
[NH2:1][C:2]1[C:10]([Br:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.CN(C(O[N:20]1N=N[C:22]2C=CC=N[C:21]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N)C.CO>O.CN(C=O)C>[NH2:1][C:2]1[C:10]([Br:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:20][CH2:21][CH3:22])=[O:6]

Participants

7

Reactant 4

HCID 887MethanolHCID 6341EthylamineHCID 2702592-Amino-3-bromobenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 82547484HCID 82547484, compoundYield 122%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-amino-3-bromo-benzoic acid (2 g, 9.26 mmol), HATU (3.84 g, 10.10 mmol, Sigma Aldrich), DMF (42.1 mL), 2.0 M ethylamine in MeOH (4.21 mL, 8.42 mmol, Sigma Aldrich), and TEA (1.8 mL, 12.62 mmol) was set stirring at RT for 18 h. It was diluted with water and extracted with EtOAc. The combined organics were dried over Na2SO4, filtered, and concentrated under reduced pressure. It was diluted with DCM, adsorbed onto silica, and purified on 40 g SiO2 (eluent: 0-100% EtOAc/hexanes over 25 min, RediSep Gold). The product fractions were combined and concentrated to give the product as a yellow oil (2.5 g, 122%). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.39 (1H, br. s.) 7.47-7.54 (2H, m) 6.52 (1H, t, J=7.82 Hz) 6.44 (2H, br. s.) 3.19-3.29 (2H, m) 1.11 (3H, t, J=7.24 Hz). m/z (ESI, +ve) 242.9 (M+H)+.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organics were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. additionIt was diluted with DCM
  6. custompurified on 40 g SiO2 (eluent: 0-100% EtOAc/hexanes over 25 min, RediSep Gold)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-83a5691cc4774213bf938f098c7e1b7d
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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