HCID 68466355, compound → Methyl α-amino-1-[(1,1-dimethylethoxy)carbonyl]-1H-indazole-5-propanoate

HRID 2355842Notes

Reaction equation

HRID 2355842 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH:17]=[C:18]([NH:23]C(OCC3C=CC=CC=3)=O)[C:19]([O:21][CH3:22])=[O:20])=[CH:14][CH:15]=2)[CH:10]=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].CO>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][CH:18]([NH2:23])[C:19]([O:21][CH3:22])=[O:20])=[CH:14][CH:15]=2)[CH:10]=[N:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 68466355HCID 68466355, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59639683Methyl α-amino-1-[(1,1-dimethylethoxy)carbonyl]-1H-indazole-5-propanoateYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 5-(2-benzyloxycarbonylamino-2-methoxycarbonyl-vinyl)-indazole-1-carboxylic acid tert-butyl ester (524 mg, 1.16 mmol) and 10% palladium on carbon (60 mg) in methanol (20 mL) was shaken for 4.5 h under 50 psi hydrogen gas using a Parr hydrogenator. The reaction mixture was evacuated and purged with nitrogen. Then, the reaction mixture was filtered through a pad of celite and the pad was rinsed with several portions of methanol. The methanol filtrate was evaporated to give the title compound (351 mg, 95%). 1H-NMR (CDCl3, 500 MHz) δ 8.12-8.10 (m, 2H), 7.55 (br s, 1H), 7.37 (dd, J=8.9, 1.5 Hz, 1H), 3.77-3.75 (m, 1H), 3.70 (s, 3H), 3.19 (dd, J=13.7, 5.5 Hz, 1H), 2.99 (dd, J=13.7, 8.0 Hz, 1H), 1.72 (s, 9H). Mass spec.: 320 (MH)+.

Workup

  1. customThe reaction mixture was evacuated
  2. custompurged with nitrogen
  3. filtrationThen, the reaction mixture was filtered through a pad of celite
  4. washthe pad was rinsed with several portions of methanol
  5. customThe methanol filtrate was evaporated

Sources & evidence

ORD record
ord-7e3320e5f5d04d52a4d69b7c980981ab
Source dataset
uspto-grants-2010_07
Patent number
US07754732B2

Reaction notes

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