Diisopropylethylamine → HCID 44540868, compound

HRID 1616010Notes

Reaction equation

HRID 1616010 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[C:5]([F:11])=[CH:4][CH:3]=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.CO>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([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:10])[C:5]([F:11])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 447547876-Chloro-3-fluoropyridine-2-carboxylic acidHCID 582680196-(1H-indol-4-yl)-1H-indazol-4-amine

Product 1

HCID 44540868HCID 44540868, compoundYield 54.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

6-Chloro-3-fluoro-2-pyridinecarboxylic acid (available from Asymchem, 848 mg, 4.83 mmol) and O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (1838 mg, 4.83 mmol) were dissolved in DMF (15 ml) and DIPEA (2.53 ml) was added. The mixture was stirred at room temperature for 30 mins. 6-(1H-indol-4-yl)-1H-indazol-4-amine (600 mg, 2.42 mmol) was added and the mixture was stirred at room temperature for 36 h. Some solvent was removed in vacuo to give ˜5 ml which was added to 2×50 g aminopropyl cartridges which had been preconditioned with methanol. The reaction mixture remained on the cartridges for 2 h before being eluted with methanol. Some solvent was removed in vacuo and a yellow precipitate crashed out which was filtered off to give the title compound (531 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 36 h
  2. customSome solvent was removed in vacuo
  3. customto give ˜5 ml which
  4. additionwas added to 2×50 g aminopropyl cartridges which
  5. waitThe reaction mixture remained on the cartridges for 2 h
  6. washbefore being eluted with methanol
  7. customSome solvent was removed in vacuo
  8. filtrationwas filtered off

Sources & evidence

ORD record
ord-cfadb2adebc14ec5abc45a3f95a84a8c
Source dataset
uspto-grants-2014_07
Patent number
US08765743B2

Reaction notes

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