2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 8-(3-Sulfamoyl-phenylamino)-thiazolo[4,5-h]quinazoline-2-carboxylic acid ethyl ester

HRID 908349Notes

Reaction equation

HRID 908349 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]2[C:17]3[N:16]=[C:15]([NH:18][C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([S:25](=[O:28])(=[O:27])[NH2:26])[CH:20]=4)[N:14]=[CH:13][C:12]=3[CH2:11][CH2:10][C:9]=2[N:29]=1)=[O:5])[CH3:2].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]2[C:17]3[N:16]=[C:15]([NH:18][C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([S:25](=[O:28])(=[O:27])[NH2:26])[CH:20]=4)[N:14]=[CH:13][C:12]=3[CH:11]=[CH:10][C:9]=2[N:29]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 592628288-(3-Sulfamoyl-phenylamino)-4,5-dihydro-thiazolo[4,5-h]quinazoline-2-carboxylic acid ethyl ester

Product 1

HCID 592629448-(3-Sulfamoyl-phenylamino)-thiazolo[4,5-h]quinazoline-2-carboxylic acid ethyl esterYield 86.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A suspension of 8-(3-Sulfamoyl-phenylamino)-4,5-dihydro-thiazolo[4,5-h]quinazoline-2-carboxylic acid ethyl ester (609 mg, 1.41 mmol) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (480 mg, 2.12 mmol) in anhydrous 1,4-dioxane (30 mL) was refluxed under nitrogen for 2 hours. The reaction mixture was cooled down to room temperature and the DDQ residues were filtered. The mother liquor was concentrated in vacuo and the resulting crude residue was triturated in a mixture of EtOAc, MeOH and DCM. The resulting solid was filtered to afford 523 mg (86% yield) of the title compound as a yellow solid. MS (ES+) 430, (ES−) 428. δH (d6 DMSO) 1.42 (3H, t), 4.51 (2H, q), 7.37 (2H, s), 7.52 (1H, d), 7.60 (1H, t), 8.09 (1H, d), 8.14 (2H, s), 8.70 (1H, s), 9.55 (1H, s), 10.59 (1H, s).

Workup

  1. temperaturewas refluxed under nitrogen for 2 hours
  2. filtrationthe DDQ residues were filtered
  3. concentrationThe mother liquor was concentrated in vacuo
  4. customthe resulting crude residue was triturated in a mixture of EtOAc, MeOH and DCM
  5. filtrationThe resulting solid was filtered

Sources & evidence

ORD record
ord-b9f2faa499294b059ef06d0d8f20fe04
Source dataset
uspto-grants-2011_09
Patent number
US08017619B2

Reaction notes

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