HCID 23290194, compound → HCID 23290185, compound

HRID 366855Notes

Reaction equation

HRID 366855 reaction equation
[N+:1]([C:4]1[C:5]([C:13]2[N:17]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:16]3[CH:24]=[CH:25][CH:26]=[CH:27][C:15]=3[N:14]=2)=[CH:6][C:7]2[O:11][CH2:10][O:9][C:8]=2[CH:12]=1)([O-])=O>[Pd].CCO>[NH2:1][C:4]1[C:5]([C:13]2[N:17]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:16]3[CH:24]=[CH:25][CH:26]=[CH:27][C:15]=3[N:14]=2)=[CH:6][C:7]2[O:11][CH2:10][O:9][C:8]=2[CH:12]=1

Participants

4

Reactant 1

HCID 23290194HCID 23290194, compound

Product 1

HCID 23290185HCID 23290185, compoundYield 10.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 1.0 g (2.71 mmol) of the ethyl 2-(6-nitro-1,3-benzodioxol-5-yl)-1H-benzimidazole-1-acetate from EXAMPLE 10 and 0.5 g of 10% palladium on carbon in 20 mL of absolute EtOH was agitated on a Parr apparatus under a hydrogen atmosphere at 32 psi for 3.5 h. The mixture was filtered through a pad of celite and concentrated to give the crude product mixture. Purification by silica gel chromatography gave 93 mg (9%) of ethyl 2-(6-amino-1,3-benzodioxol-5-yl)-1H-benzimidazole-1-acetate as a solid: mp 284.2-287° C.; 1H NMR (CDCl3) δ 1.29 (t, J=7.2 Hz, 3H), 4.27 (q, J=7.1 Hz, 2H), 4.85 (s, 2H), 5.93 (s, 2H), 6.38 (s, 1H), 6.79 (s, 1H), 7.26-7.40 (m, 3H), 7.73-7.83 (m, 1H); HRMS (FAB) Calc'd for M+H: 340.1297, found: 340.1255.

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. concentrationconcentrated
  3. customto give the crude product mixture
  4. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-43265e9b273246ec84e519df8252c6ec
Source dataset
uspto-grants-2000_10
Patent number
US06130333

Reaction notes

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