Triethylamine → HCID 86711679, compound

HRID 710655Notes

Reaction equation

HRID 710655 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[CH2:15][CH2:14][CH2:13][NH:12][C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[I:17][C:18]1[CH:19]=[N:20][N:21]([CH2:23][C:24](O)=[O:25])[CH:22]=1.CCN(CC)CC.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[CH2:15][CH2:14][CH2:13][N:12]([C:24](=[O:25])[CH2:23][N:21]4[CH:22]=[C:18]([I:17])[CH:19]=[N:20]4)[C:11]=3[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 195766471H-pyrazole-1-acetic acid, 4-iodo-HCID 679846101-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 86711679HCID 86711679, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine (0.400 g, 1.83 mmol), 2-(4-iodo-pyrazol-1-yl)acetic acid (0.554 g, 2.2 mmol) and NEt3 (0.642 mL, 4.59 mmol) in DMF (5 mL) was added HATU (0.836 g, 2.2 mmol). The mixture was stirred at rt for 40 min. It was then quenched with water. The mixture was partitioned between EtOAc (100 mL) and sat. NaHCO3 (50 mL). The organic layer was separated, dried over Na2SO4, concentrated in vacuo, and purified by flash chromatography (SiO2, with a gradient elution of 0˜30% EtOAc/CH2Cl2) to yield 1-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]-2-(4-iodopyrazol-1-yl)ethanone (0.82 g, 100%).

Workup

  1. customIt was then quenched with water
  2. customThe mixture was partitioned between EtOAc (100 mL) and sat. NaHCO3 (50 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography (SiO2
  7. washwith a gradient elution of 0˜30% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-9c62d5aeb1a743e684952479da46c1d4
Source dataset
uspto-grants-2015_11
Patent number
US09181241B2

Reaction notes

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