HCID 10906711, compound → 2-(2-Oxo-piperazin-1-ylmethyl)-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester

HRID 1432920Notes

Reaction equation

HRID 1432920 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[CH:15]=[CH:14][N:13]=[CH:12][C:11]=2[CH:10]=[C:9]1[CH2:17][N:18]1[CH2:23][CH2:22][N:21](C(OCC2C=CC=CC=2)=O)[CH2:20][C:19]1=[O:34])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)=O.CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[C:16]2[CH:15]=[CH:14][N:13]=[CH:12][C:11]=2[CH:10]=[C:9]1[CH2:17][N:18]1[CH2:23][CH2:22][NH:21][CH2:20][C:19]1=[O:34])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 10906711HCID 10906711, compound

Product 1

HCID 544278362-(2-Oxo-piperazin-1-ylmethyl)-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl esterYield 67.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 18963719Formic acid methanolSolvent

Procedure

Palladium black (1.1 g, 10.3 mmol) is added to a solution of 2-(4-benzyloxycarbonyl-2-oxo-piperazin-1-ylmethyl)pyrrolo[3,2-c]pyridin-1-carboxylic acid tert-butyl ester (1.7 g, 3.7 mmol) in HCO2H/MeOH (45 mL, 4.4% solution). After 40 minutes the catalyst is filtered through Celite and washed with MeOH. The filtrate is concentrated in vacuo to remove methanol then the resulting solution is diluted with methylene chloride and washed with saturated sodium bicarbonate, and brine. The organic layer is dried over MgSO4, filtered and concentrated to dryness. The resulting solid is purified by column chromatography eluting with a gradient of 5% MeOH/CH2Cl2 to 10% MeOH/CH2Cl2 to give the product (0.8 g, 2.5 mmol) as a pale yellow foamy solid. 1H NMR (CDCl3, 300 MHz) δ8.78 (s, 1H), 8.40 (d, 1H), 7.9 (d, 1H), 6.48 (s, 1H), 4.98 (s, 2H), 3.7 (s, 2H), 3.51 (t, 2H), 3.40 (t, 2H), 1.91 (bs, 1H), 1.70 (s, 9H).

Workup

  1. filtrationAfter 40 minutes the catalyst is filtered through Celite
  2. washwashed with MeOH
  3. concentrationThe filtrate is concentrated in vacuo
  4. customto remove methanol
  5. additionthe resulting solution is diluted with methylene chloride
  6. washwashed with saturated sodium bicarbonate, and brine
  7. dry with materialThe organic layer is dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated to dryness
  10. customThe resulting solid is purified by column chromatography
  11. washeluting with a gradient of 5% MeOH/CH2Cl2 to 10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-aa873a6dba394caeb3b078d13145c313
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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