Bis-(1H-imidazol-2-YL)-methanone → HCID 117601782, compound

HRID 1773757Notes

Reaction equation

HRID 1773757 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:12]=[C:11]([NH2:13])[C:10]([NH2:14])=[C:9]([I:15])[CH:8]=2)=[C:5]([CH3:16])[O:4][N:3]=1.[C:17](C1NC=CN=1)(C1NC=CN=1)=[O:18]>CN(C1C=CN=CC=1)C.C1COCC1>[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]([I:15])[C:10]3[NH:14][C:17](=[O:18])[NH:13][C:11]=3[CH:12]=2)=[C:5]([CH3:16])[O:4][N:3]=1

Participants

5

Reactant 2

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 117601490HCID 117601490, compound

Product 1

HCID 117601782HCID 117601782, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

5-(3,5-dimethylisoxazol-4-yl)-3-iodobenzene-1,2-diamine (253 g, 0.77 mol, 1.0 eq) was treated with carbonyl diimidazole (187 g, 1.15 mol, 1.5 eq) and DMAP (47 g, 384 mmol, 0.5 eq) in THF (2.5 L) at 80° C. for 16 h. The precipitate was obtained by filtration. The solid was triturated with EA/PE (1/1) to give 197 g of 6-(3,5-dimethylisoxazol-4-yl)-4-iodo-1H-benzo[d]imidazol-2(3H)-one as a white solid.

Workup

  1. customThe precipitate was obtained by filtration
  2. customThe solid was triturated with EA/PE (1/1)

Sources & evidence

ORD record
ord-ce719e2e3f0d4a5d9125c19b5d80fd8a
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

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