Triethylamine → HCID 66977452, compound

HRID 77090

Reaction equation

HRID 77090 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[N+:43]([C:46]1[CH:51]=[CH:50][N:49]=[CH:48][C:47]=1[NH2:52])([O-:45])=[O:44]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7]([NH:52][C:47]1[CH:48]=[N:49][CH:50]=[CH:51][C:46]=1[N+:43]([O-:45])=[O:44])=[O:9]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 331275-Bromo-2-chlorobenzoic acidHCID 5869433-Amino-4-nitropyridineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 66977452HCID 66977452, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

Method C—Step a To a mixture of 5-Bromo-2-chlorobenzoic acid (5.00 g, 21.23 mmol) in DMF (40 mL), HATU (8.48 g, 22.29 mmol) and triethylamine (2.97 mL, 21.44 mmol) were added. After 30 min stirring at room temperature 4-nitro-pyridin-3ylamine (2.36 g, 16.99 mmol) was added, the reaction mixture stirred at 40° C. overnight and solvent removed. The crude was then diluted with EtOAc (40 mL) and washed first with saturated Na2CO3 solution (6×30 mL) then 1N HCl (3×30 mL). The organic layer was dried over Na2SO4, filtered and left standing. The precipitate obtained was filtered to get 4.75 g of the title compound (63%).

Workup

  1. additionwere added
  2. additionwas added
  3. customsolvent removed
  4. additionThe crude was then diluted with EtOAc (40 mL)
  5. washwashed first with saturated Na2CO3 solution (6×30 mL)
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. waitleft
  9. customThe precipitate obtained
  10. filtrationwas filtered

Sources & evidence

ORD record
ord-8414b45ac20546a680e832ed55f2f1d1
Source dataset
uspto-grants-2014_09
Patent number
US08835648B2

Linked notes

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