HCID 67285786, compound → HCID 66599421, compound

HRID 1909046Notes

Reaction equation

HRID 1909046 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][CH:8]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[C:15]([NH2:22])[N:14]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>[Pd].CCO>[C:1]([O:5][C:6](=[O:23])[NH:7][CH:8]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[C:15]([NH2:22])[N:14]=2)[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 67285786HCID 67285786, compound

Product 1

HCID 66599421HCID 66599421, compoundYield 282.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The mixture of [1-(6-amino-5-nitro-pyridin-2-yl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester (2 g, 2.17 mmole), Pd/C (148 mg, 1.23 mmole), and EtOH (100 ml) was shaken under H2 gas for 2 days. Reaction solution was filtered and filtrate was concentrated to afford [1-(5,6-diamino-pyridin-2-yl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester (1.8 g, ˜100%) as a dark green solid. 1H NMR (400 MHz, CD3OD) δ 1.17 (m, 1H), 1.44 (s, 9H), 1.86 (m, 16H), 2.18 (m, 12H), 3.14 (m, 1H), 3.42 (m, 1H), 3.59 (m, 1H), 4.505 (m, 1H), 6.67 (d, J=6.53 Hz, 1H), 6.920 (m, 1H). MS(ESI) m/z 294 [M+1].

Workup

  1. customReaction solution
  2. filtrationwas filtered
  3. concentrationfiltrate was concentrated

Sources & evidence

ORD record
ord-460d97de79a8410cb8001fa82ecc58a9
Source dataset
uspto-grants-2013_12
Patent number
US08598217B2

Reaction notes

Loading…