Imidazole → HCID 117601782, compound

HRID 1773760Notes

Reaction equation

HRID 1773760 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].N1C=CN=C1>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

6

Reactant 3

HCID 795ImidazoleHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 117601490HCID 117601490, compound

Product 1

HCID 117601782HCID 117601782, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-(3,5-dimethylisoxazol-4-yl)-3-iodobenzene-1,2-diamine (15 g, 45.6 mmol, 1.0 eq), DMAP (2.9 g, 22.7 mmol, 0.5 eq) and carbonyl diimidazole (11.0 g, 68.4 mmol, 1.5 eq) in THF (200 mL) was refluxed for 3 h. The reaction was cooled to room temperature, purified by flash column chromatography to give a solid, which contained some imidazole and DMAP. The solid was triturated with THF (2×) and filtered to afford 6-(3,5-dimethylisoxazol-4-yl)-4-iodo-1H-benzo[d]imidazol-2(3H)-one. LC-MS: 354.0 [M−H]−1H NMR (400 MHz, DMSO-d6) δ 10.9 (br s, 2H), 7.24 (d, J=1.6 Hz, 1H), 6.97 (d, J=1.6 Hz, 1H), 2.37 (s, 3H), 1.78 (s, 3H).

Workup

  1. temperaturewas refluxed for 3 h
  2. custompurified by flash column chromatography
  3. customto give a solid, which
  4. customThe solid was triturated with THF (2×)
  5. filtrationfiltered

Sources & evidence

ORD record
ord-25711caf2ac64e769ba8ad025caac50f
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

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