Acetic Acid → HCID 178478655, compound

HRID 1263539

Reaction equation

HRID 1263539 reaction equation
[N+:1]([C:4]1[C:5]([NH2:11])=[C:6]([NH2:10])[CH:7]=[CH:8][CH:9]=1)([O-])=O.[NH2:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=1[NH2:22])[C:16]([OH:18])=[O:17].[ClH:23].Cl.[C:25](=N)(OCC)[CH2:26][C:27](=N)OCC.C(O)(=O)C>Cl>[ClH:23].[ClH:23].[NH2:10][C:6]1[C:5]2[N:11]=[C:25]([CH2:26][C:27]3[NH:22][C:21]4[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][C:13]=4[N:12]=3)[NH:1][C:4]=2[CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 692633,4-Diaminobenzoic acidHCID 73106Diethyl malonimidateHCID 43595253-Nitro-1,2-phenylenediamine

Product 1

HCID 178478655HCID 178478655, compoundYield 31.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The following components were reacted according to General Procedure 1, above: 3-nitro-1,2-phenylenediamine (0.50 g; 3.26 mmoles) 3,4-diaminobenzoic acid (0.40 g; 3.26 mmoles), diethyl malonimidate dihydrochloride (1.1 eq.; 0.83 g; 3.60 mmoles) and acetic acid (25 mL). The crude mixture of three compounds was then reduced according to General Procedure 2, above. The crude solid product was taken up in 10 mL of dilute HCl, purified by preparative HPLC (2 to 40% acetonitrile (with 0.1% TFA) over 60 minutes) and converted to the HCl salt by three freeze drying cycles with dilute HCl. This procedure gave 0.213 g of pure 2-[(4-amino-1H-benzimidazol-2-yl)methyl]-1H-benzimidazole-5-carboxylic acid dihydrochloride in 17% yield. It had MS: m/z=308.2 [M+1] amu and gave one peak on HPLC at both 210 and 280 nm (10.20 minutes using the JWTFACN gradient).

Workup

  1. customThe following components were reacted
  2. additionThe crude mixture of three compounds
  3. custompurified by preparative HPLC (2 to 40% acetonitrile (with 0.1% TFA) over 60 minutes)
  4. dry with materialdrying cycles with dilute HCl

Sources & evidence

ORD record
ord-1e3d270b009b4acdaaeaa9719194720a
Source dataset
uspto-grants-2003_04
Patent number
US06541486B1

Linked notes

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