1,1'-Carbonyldiimidazole → HCID 90054926, compound

HRID 1772986Notes

Reaction equation

HRID 1772986 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:3]=1[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][C:7]=1[S:12]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=1)(=[O:14])=[O:13].[C:31](N1C=CN=C1)(N1C=CN=C1)=[O:32]>ClCCCl>[Cl:1][C:2]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:3]=1[CH2:4][N:5]1[C:6]2[CH:11]=[CH:10][N:9]=[CH:8][C:7]=2[S:12](=[O:14])(=[O:13])[N:15]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=2)[C:31]1=[O:32]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 90022747HCID 90022747, compound

Product 1

HCID 90054926HCID 90054926, compoundYield 22.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 4-[(2-chloro-6-fluorobenzyl)amino]-N-(3,4-di methoxyphenyl)pyridine-3-sulfonamide (0.04 g, 0.09 mmol) and 1,1′-carbonyldiimidazole (56 mg, 0.34 mmol) in 1,2-dichloroethane (10 mL) was heated for 30 min at 100° C., then cooled and concentrated in vacuo. Purification by gradient column chromatography eluting with 0-30% EtOAc in hexane yielded the title compound (10 mg, 0.02 mmol).

Workup

  1. temperaturecooled
  2. concentrationconcentrated in vacuo
  3. customPurification by gradient column chromatography
  4. washeluting with 0-30% EtOAc in hexane

Sources & evidence

ORD record
ord-a59107e4f5cc484294870a46f27317e4
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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