1,1'-Carbonyldiimidazole → 2-(4-[1,3] Dioxolan-2-yl-2-fluorophenyl)-1h-benzimidazole-4-carboxamide

HRID 2374685Notes

Reaction equation

HRID 2374685 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:14]=[CH:13][C:9]([C:10](O)=O)=[C:8]([F:15])[CH:7]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.Cl.[NH2:30][C:31]1[C:39]([NH2:40])=[CH:38][CH:37]=[CH:36][C:32]=1[C:33]([NH2:35])=[O:34]>N1C=CC=CC=1.CN(C)C=O>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:14]=[CH:13][C:9]([C:10]2[NH:40][C:39]3[CH:38]=[CH:37][CH:36]=[C:32]([C:33]([NH2:35])=[O:34])[C:31]=3[N:30]=2)=[C:8]([F:15])[CH:7]=1

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 534228072,3-Diaminobenzamide dihydrochlorideHCID 673539164-(1,3-Dioxolan-2-yl)-2-fluorobenzoic acid

Product 1

HCID 673529522-(4-[1,3] Dioxolan-2-yl-2-fluorophenyl)-1h-benzimidazole-4-carboxamideYield 22%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of EXAMPLE 20D (1.5 g, 7.1 mmol) in pyridine (5 mL) and N,N-dimethylformamide (20 mL) was treated with 1,1′-carbonyldiimidazole (1.4 g, 8.5 mmol) at 40° C. for 30 minutes. 2,3-Diaminobenzamide dihydrochloride (synthesized as described in U.S. Pat. No. 6,737,421, column 11, EXAMPLE 2, step (e), 1.58 g, 7.1 mmol) was added and the mixture stirred at ambient temperature overnight. Solvents were removed and the residue suspended in 10 mL of acetic acid. The mixture was stirred at 80° C. overnight, cooled, and concentrated and the residue was purified by flash chromatography using ethyl acetate to give the title compound (500 mg, 22%). MS (DCI/NH3) m/z 329 (M+H)+.

Workup

  1. addition6,737,421, column 11, EXAMPLE 2, step (e), 1.58 g, 7.1 mmol) was added
  2. customSolvents were removed
  3. stirringThe mixture was stirred at 80° C. overnight
  4. temperaturecooled
  5. concentrationconcentrated
  6. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-0941408ce7024a47a935ba4d6ca7afc6
Source dataset
uspto-grants-2008_12
Patent number
US07462724B2

Reaction notes

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