Pyrrolidine → HCID 68715634, compound

HRID 2380836Notes

Reaction equation

HRID 2380836 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][NH:9][C:10](=[O:14])[C:11]([OH:13])=O)[CH:3]=1.[CH:15]([N:18]([CH:21]([CH3:23])C)CC)([CH3:17])C.N1CCCC1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O>[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][NH:9][C:10](=[O:14])[C:11](=[O:13])[N:18]2[CH2:15][CH2:17][CH2:23][CH2:21]2)[CH:3]=1

Participants

6

Reactant 4

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68712583Ethanedioic acid, 1-[2-(4-iodo-2-pyridinyl)hydrazide]

Product 1

HCID 68715634HCID 68715634, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of [2-(4-iodopyridin-2-yl)hydrazino](oxo)acetic acid (0.64 g, 2.10 mmol) in di-methylformamide (21 mL) was added diisopropylethylamine (1.65 mL, 9.47 mmol), pyrrolidine (0.74 mL, 8.84 mmol) and finally HATU (2.40 g, 6.31 mmol). The resulting mixture was stirred at room temperature under argon atmosphere for 18 hours. The solvent was removed under reduced pressure, water was added and it was extracted with ethyl acetate. The combined organic layers were washed with brine, dried and concentrated. The crude was purified by reverse phase chromatography on a silica C18 cartridge eluting with water/acetonitrile:methanol (1:1), using a gradient from 100% water to 100% acetonitrile:methanol (1:1), to yield the title compound (0.26 g, 30%) as a white solid.

Workup

  1. customThe solvent was removed under reduced pressure, water
  2. additionwas added
  3. extractionit was extracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customThe crude was purified by reverse phase chromatography on a silica C18 cartridge
  8. washeluting with water/acetonitrile

Sources & evidence

ORD record
ord-d264cf19f88f43cc8bd570fcfec8c46f
Source dataset
uspto-grants-2012_09
Patent number
US08258122B2

Reaction notes

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