Methanol → HCID 178452967, compound

HRID 2114996Notes

Reaction equation

HRID 2114996 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1[NH:12][C:11]2[CH:13]=[CH:14][C:15]([N+:17]([O-])=O)=[CH:16][C:10]=2[N:9]=1)([CH3:4])([CH3:3])[CH3:2].CO>[Pd].O1CCCC1>[C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1[NH:12][C:11]2[CH:13]=[CH:14][C:15]([NH2:17])=[CH:16][C:10]=2[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 887MethanolHCID 69100214HCID 69100214, compoundHCID 178452969HCID 178452969, compound

Product 1

HCID 178452967HCID 178452967, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 13.3 g (47.8 mmol) of (5-nitro-1H-benzoimidazol-2-yl)-carbamic acid tert-butyl ester and (6-nitro-1H-benzimidazol-2-yl)-carbamic acid tert-butyl ester, 100 ml of methanol, 100 ml of tetrahydrofuran and 1 g of 10% Pd/C catalyst is hydrogenated. After completion of the reaction, the catalyst is filtered off, washed with tetrahydrofuran and the filtrate is concentrated. The residue is purified by column chromatography using Kieselgel 60 (Merck) as adsorbent and chloroform:methanol=10:1 as eluent to yield 4.72 g (40.4%) of (6-amino-1H-benzoimidazol-2-yl)-carbamic acid tert-butyl ester (Rf. 0.5), Melting Point: 159° C. (diethyl ether) and 4.2 g (36.0%) of (5-amino-1H-benzoimidazol-2-yl)-carbamic acid tert-butyl ester (Rf. 0.4) Melting Point: 168° C. (diethyl ether)

Workup

  1. customAfter completion of the reaction
  2. filtrationthe catalyst is filtered off
  3. washwashed with tetrahydrofuran
  4. concentrationthe filtrate is concentrated
  5. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-2f20ce25872b40529bd132ffde5ca094
Source dataset
uspto-grants-2008_10
Patent number
US07435744B2

Reaction notes

Loading…