Pyridine → HCID 23571042, compound

HRID 1823899Notes

Reaction equation

HRID 1823899 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH:17][C:18](=[O:32])[CH:19]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=3)OS(C)(=O)=O)=[CH:14][CH:15]=2)[CH:10]=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[C:39]([O:43][C:44](=[O:49])[NH:45][CH2:46][CH2:47][NH2:48])([CH3:42])([CH3:41])[CH3:40]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH:17][C:18](=[O:32])[CH:19]([NH:48][CH2:47][CH2:46][NH:45][C:44]([O:43][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:49])[C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=3)=[CH:14][CH:15]=2)[CH:10]=[N:9]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 187201N-BOC-ethylenediamineHCID 53630239HCID 53630239, compound

Product 1

HCID 23571042HCID 23571042, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 5-[2-(3-chloro-phenyl)-2-methanesulfonyloxy-acetylamino]-indazole-1-carboxylic acid tert-butyl ester (1.49 mmol) in dry THF (4 mL) was added pyridine (4.48 mmol, 3 equivalents) followed by followed by a dry THF solution of (2-amino-ethyl)-carbamic acid tert-butyl ester (3 equivalents, ˜0.5 mL/mmol). The resulting solution was refluxed at 60° C. overnight. The reaction mixture was then concentrated in vacuo and the resulting oil was partitioned between EtOAc and brine. The organic layer was washed with brine (thrice), dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography using eluting with EtOAc:hexane (60:40) to afford the title compound in 85% yield.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe resulting oil was partitioned between EtOAc and brine
  3. washThe organic layer was washed with brine (thrice)
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography
  8. washusing eluting with EtOAc:hexane (60:40)

Sources & evidence

ORD record
ord-2d870fc546bb488bb79ce4e4bf3281b4
Source dataset
uspto-grants-2006_05
Patent number
US07041687B2

Reaction notes

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