Isonicotinic Acid → HCID 58483587, compound

HRID 68688Notes

Reaction equation

HRID 68688 reaction equation
Cl.[CH3:2][S:3][C:4]1[C:12]2[C:7](=[CH:8][C:9]([N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)=[CH:10][CH:11]=2)[N:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:5]=1.C(N(CC)CC)C.[C:32](O)(=[O:39])[C:33]1[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O.C(OCC)(=O)C>[CH3:2][S:3][C:4]1[C:12]2[C:7](=[CH:8][C:9]([N:13]3[CH2:14][CH2:15][N:16]([C:32]([C:33]4[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=4)=[O:39])[CH2:17][CH2:18]3)=[CH:10][CH:11]=2)[N:6]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:5]=1

Participants

7

Reactant 4

HCID 5922Isonicotinic AcidHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 674482143-(methylthio)-1-phenyl-6-(piperazin-1-yl)-1H-indazole hydrochloride

Product 1

HCID 58483587HCID 58483587, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Into a 50-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 3-(methylthio)-1-phenyl-6-(piperazin-1-yl)-1H-indazole hydrochloride (200 mg, 0.55 mmol, 1.00 equiv) in N,N-dimethylformamide (5 mL), triethylamine (140.3 mg, 1.39 mmol, 2.51 equiv), isonicotinic acid (82 mg, 0.67 mmol, 1.20 equiv), and the resulting solution was stirred for 10 min at room temperature. HATU (631 mg, 1.66 mmol, 3.00 equiv) was added and resulting solution was stirred for an additional 2 h at room temperature. The resulting solution was diluted with ethyl acetate (20 mL). The resulting mixture was washed with brine (2×15 mL). The resulting mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate:petroleum ether:THF (1:1:1) to yield (4-(3-(methylthio)-1-phenyl-1H-indazol-6-yl)piperazin-1-yl)(pyridin-4-yl)methanone as a light yellow solid.

Workup

  1. customInto a 50-mL 3-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. customresulting solution
  4. stirringwas stirred for an additional 2 h at room temperature
  5. washThe resulting mixture was washed with brine (2×15 mL)
  6. dry with materialThe resulting mixture was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-78c696b6b98c4cafb1a0b6775d83b27e
Source dataset
uspto-grants-2014_09
Patent number
US08822447B2

Reaction notes

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