Tetrahydrofuran → HCID 117601430, compound

HRID 1773669Notes

Reaction equation

HRID 1773669 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=C(N)C(NC)=[C:11]([I:13])[CH:12]=2)=[C:5]([CH3:17])[O:4][N:3]=1.C1N=CN([C:23]([N:25]2[CH:29]=[N:28][CH:27]=[CH:26]2)=O)C=1.C1C[O:33]CC1>>[CH3:1][C:2]1[C:6]([C:7]2[CH:12]=[C:11]([I:13])[C:26]3[N:25]([CH3:23])[C:29](=[O:33])[NH:28][C:27]=3[CH:8]=2)=[C:5]([CH3:17])[O:4][N:3]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 117601757HCID 117601757, compound

Product 1

HCID 117601430HCID 117601430, compound

Conditions

Temperature
120 °C

Procedure

Into a flask containing 4-(3,5-dimethylisoxazol-4-yl)-6-iodo-N1-methylbenzene-1,2-diamine (299 mg, 0.87 mmol, 1 equiv) is added THF (8 mL, 0.1 M) and CDI (282 mg, 1.74 mmol, 2 equiv). The reaction was heated for 2 hr at 120° C. The reaction was then concentrated in vacuo and the solid triturated with diethyl ether before being air dried to furnish 5-(3,5-dimethylisoxazol-4-yl)-7-iodo-1-methyl-1H-benzo[d]imidazol-2(3H)-one as a light yellow solid.

Workup

  1. concentrationThe reaction was then concentrated in vacuo
  2. customthe solid triturated with diethyl ether
  3. customdried

Sources & evidence

ORD record
ord-dd195947a27c4d1eb223612620f99cc0
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

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