Triethylamine → HCID 66701605, compound

HRID 1186768Notes

Reaction equation

HRID 1186768 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:11]([CH3:20])[C:12](=[O:19])[CH:13]=[CH:14][C:15]=1C(O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:28])C=CC=CC=1.C([N:40]([CH2:43]C)CC)C>C(#N)C>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:10]2[N:11]([CH3:20])[C:12](=[O:19])[CH:13]=[CH:14][C:15]=2[NH:40][C:43]1=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 66701592HCID 66701592, compound

Product 1

HCID 66701605HCID 66701605, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

2-[(2-fluoro-4-iodophenyl)amino]-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid (5.840 g, 15 mmol) was suspended in acetonitrile (117 ml) and diphenylphosphoryl azide (1.2 eq., 4 ml, 18 mmol) as well as triethylamine (1.2 eq., 2.5 ml, 18 mmol) were added. The mixture was stirred at 60° C. for 5 hours. A suspension was formed. The precipitate was filtered off and washed once with acetonitrile and dried in vacuo. The residue delivered the title product (4.20 g, 69%) sufficient purity (95% UV) and was used for the next transformation without further purification.

Workup

  1. customA suspension was formed
  2. filtrationThe precipitate was filtered off
  3. washwashed once with acetonitrile
  4. customdried in vacuo
  5. customwas used for the next transformation without further purification

Sources & evidence

ORD record
ord-14e5741d997640a2be69e962958adf08
Source dataset
uspto-grants-2014_03
Patent number
US08673919B2

Reaction notes

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