Clopyralid → HCID 44540871, compound

HRID 1616020Notes

Reaction equation

HRID 1616020 reaction equation
[Cl:1][C:2]1[C:3]([C:9]([OH:11])=O)=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[NH:45]1[C:53]2[C:48](=[C:49]([C:54]3[CH:55]=[C:56]([NH2:63])[C:57]4[CH:58]=[N:59][NH:60][C:61]=4[CH:62]=3)[CH:50]=[CH:51][CH:52]=2)[CH:47]=[CH:46]1>CN(C=O)C>[Cl:1][C:2]1[C:3]([C:9]([NH:63][C:56]2[CH:55]=[C:54]([C:49]3[CH:50]=[CH:51][CH:52]=[C:53]4[C:48]=3[CH:47]=[CH:46][NH:45]4)[CH:62]=[C:61]3[C:57]=2[CH:58]=[N:59][NH:60]3)=[O:11])=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 15553ClopyralidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 582680196-(1H-indol-4-yl)-1H-indazol-4-amine

Product 1

HCID 44540871HCID 44540871, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3,6-dichloro-2-pyridinecarboxylic acid (available from Matrix Scientific, 930 mg, 4.8 mmol) and O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (1840 mg, 4.8 mmol) were dissolved in DMF (15 ml) and treated with DIPEA (2.53 ml). The mixture was stirred at room temperature for 30 mins then 6-(1H-indol-4-yl)-1H-indazol-4-amine (600 mg, 2.4 mmol) was added and the mixture stirred at room temperature overnight. The reaction mixture was concentrated in vacuo to approx. 5 ml which was added to 2×50 g aminopropyl cartridges that had been preconditioned with MeOH. The reaction mixture remained on the cartridges for 3 h before being eluted with MeOH. The mixture was concentrated in vacuo and a precipitate occurred, which was collected by filtration to give the title compound (0.55 g) as a yellow solid.

Workup

  1. stirringthe mixture stirred at room temperature overnight
  2. concentrationThe reaction mixture was concentrated in vacuo to approx. 5 ml which
  3. additionwas added to 2×50 g aminopropyl cartridges that
  4. waitThe reaction mixture remained on the cartridges for 3 h
  5. washbefore being eluted with MeOH
  6. concentrationThe mixture was concentrated in vacuo
  7. filtrationwhich was collected by filtration

Sources & evidence

ORD record
ord-b9ebd53fd46c43c39ee87421e84db859
Source dataset
uspto-grants-2014_07
Patent number
US08765743B2

Reaction notes

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