HCID 68289091, compound → 6-(Pyrrolidin-1-YL)pyridine-3,4-diamine

HRID 541201Notes

Reaction equation

HRID 541201 reaction equation
[N+:1]([C:4]1[C:5]([NH2:15])=[CH:6][C:7]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[N:8][CH:9]=1)([O-])=O>[Pd]>[N:10]1([C:7]2[N:8]=[CH:9][C:4]([NH2:1])=[C:5]([NH2:15])[CH:6]=2)[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

3

Reactant 1

HCID 68289091HCID 68289091, compound2×

Product 1

HCID 682882956-(Pyrrolidin-1-YL)pyridine-3,4-diamineYield 94%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a 100 mL round bottom flask was added 5-nitro-2-(pyrrolidin-1-yl)pyridin-4-amine (compound 20.1, 800 mg, 3.84 mmol, 1.0 equiv) and Pd on carbon (10 wt % Pd, 400 mg, 0.38 mmol, 0.1 equiv). The system was purged with nitrogen and charged with methanol (19 mL) followed by hydrogen. The mixture was stirred at room temperature under hydrogen for 4 hours then purged with nitrogen. The mixture was filtered though celite and washed extensively with MeOH. The solvents were removed in vacuo to obtain the title compound as a purple solid (641 mg, 94%). m/z (ES+) 179.3 (M+H)+. 1H NMR (400 MHz, DMSO-d6): δ 7.27 (s, 1H), 5.62 (s, 1H), 5.14 (br s, 2H), 3.67 (br s, 2H), 3.23-3.13 (m, 4H), 1.91-1.79 (m, 4H).

Workup

  1. customThe system was purged with nitrogen
  2. additioncharged with methanol (19 mL)
  3. customthen purged with nitrogen
  4. filtrationThe mixture was filtered though celite
  5. washwashed extensively with MeOH
  6. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-2f450776cecd40d79036bcf5e02c34aa
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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