Hydrochloric Acid → HCID 67128629, compound

HRID 1927579Notes

Reaction equation

HRID 1927579 reaction equation
[CH3:1][CH2:2][N:3](C(C)C)[CH:4](C)[CH3:5].[N+:10]([C:13]1[CH:21]=[CH:20][CH:19]=[C:15]([C:16]([OH:18])=O)[C:14]=1[OH:22])([O-:12])=[O:11].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(NCC)C.Cl>CN(C=O)C>[CH2:2]([N:3]([CH2:4][CH3:5])[C:16](=[O:18])[C:15]1[CH:19]=[CH:20][CH:21]=[C:13]([N+:10]([O-:12])=[O:11])[C:14]=1[OH:22])[CH3:1]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 68073-Nitrosalicylic acidHCID 8021DiethylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 67128629HCID 67128629, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1.19 ml of DIPEA are added to a stirring dispersion of 0.5 g 3-nitrosalicyclic acid and 1.14 g of HATU in 4 ml of DMF at rt under an inert atmosphere of nitrogen. After stirring at it for 1 minute, 0.31 ml of diethylamine in 1 ml of dry DMF are added. After stirring at it for 1 hour, a reaction mixture obtained is added to 50 ml of 1M HCl and extracted with 50 ml EtOAc. Solvent is evaporated and a residue obtained is purified by chromatography on silca eluting with 2:1 iso-hexane/EtOAc. The title compound is obtained. MH+ 239.

Workup

  1. stirringAfter stirring at it for 1 hour
  2. customa reaction mixture obtained
  3. extractionextracted with 50 ml EtOAc
  4. customSolvent is evaporated
  5. customa residue obtained
  6. customis purified by chromatography
  7. washon silca eluting with 2:1 iso-hexane/EtOAc

Sources & evidence

ORD record
ord-9005b901e94f40fea1198bf09b3753f9
Source dataset
uspto-grants-2012_05
Patent number
US08183281B2

Reaction notes

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