HCID 22181416, compound → HCID 22181263, compound

HRID 1796525Notes

Reaction equation

HRID 1796525 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3=[N:10][CH:11]=[C:12]([N+:14]([O-])=O)[CH:13]=[C:8]3[N:7]=[C:6]2[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH3:26])=[CH:20][CH:19]=2)[CH2:3][CH2:2]1>CCOC(C)=O.C(O)(=O)C.[Pd]>[CH:1]1([CH2:4][N:5]2[C:9]3=[N:10][CH:11]=[C:12]([NH2:14])[CH:13]=[C:8]3[N:7]=[C:6]2[CH2:17][C:18]2[CH:19]=[CH:20][C:21]([O:24][CH2:25][CH3:26])=[CH:22][CH:23]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 1

HCID 22181416HCID 22181416, compound

Product 1

HCID 22181263HCID 22181263, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(cyclopropylmethyl)-2-[(4-ethoxyphenyl)methyl]-6-nitro-3H-imidazo[4,5-b]pyridine (1.35 g, 3.84 mmol) in EtOAc (20 mL) and acetic acid (1 mL) at room temperature was added Pd/C (308 mg, 10% grade). The mixture was placed in a Parr apparatus under 35 psi H2. The mixture was shaken for 72 hours. The reaction was filtered over Celite. The filtrate was taken up into 1 M NaOH aqueous solution (25 mL) and EtOAc (50 mL) and the phases separated. The aqueous phase was back-extracted with additional EtOAc (2×50 mL). The organic phases were combined, dried with MgSO4, filtered and concentrated in vacuo. The process gave 1.18 g of the title compound 3-(cyclopropylmethyl)-2-[(4-ethoxyphenyl)methyl]-3H-imidazo[4,5-b]pyridin-6-amine (95% yield from 3-(cyclopropylmethyl)-2-[(4-ethoxyphenyl)methyl]-6-nitro-3H-imidazo[4,5-b]pyridine), with purity>95% by HPLC analysis. The residue was used without further purification. 1H-NMR (400 MHz, CDCl3): δ 0.35 (m, 2H), 0.46 (m, 2H), 1.11 (m, 1H), 1.39 (t, J=6.8 Hz, 3H), 3.26 (br s, 2H), 3.98 (m, 4H), 4.25 (s, 2H), 6.83 (d, J=8.8 Hz, 2H), 7.16 (d, J=8.8 Hz, 2H), 7.34 (d, J=2.3 Hz, 1H), 7.87 (d, J=2.3 Hz, 1H). MS (ESI) (M+H)+: 323.

Workup

  1. filtrationThe reaction was filtered over Celite
  2. customthe phases separated
  3. extractionThe aqueous phase was back-extracted with additional EtOAc (2×50 mL)
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-18b2cba421bb40c19b616782b8ec21ad
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

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