2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → (2-Methyl-thiazolo[4,5-h]quinazolin-8-yl)-phenyl-amine

HRID 2102794Notes

Reaction equation

HRID 2102794 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[C:13]3[N:12]=[C:11]([NH:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[N:10]=[CH:9][C:8]=3[CH2:7][CH2:6][C:5]=2[N:21]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1(C)C=CC=CC=1.CCOC(C)=O>[CH3:1][C:2]1[S:3][C:4]2[C:13]3[N:12]=[C:11]([NH:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[N:10]=[CH:9][C:8]=3[CH:7]=[CH:6][C:5]=2[N:21]=1

Participants

5

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 11150562(2-Methyl-4,5-dihydro-thiazolo[4,5-h]quinazolin-8-yl)-phenyl-amine

Product 1

HCID 11346863(2-Methyl-thiazolo[4,5-h]quinazolin-8-yl)-phenyl-amineYield 43%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

(2-Methyl-4,5-dihydro-thiazolo[4,5-h]quinazolin-8-yl)-phenyl-amine (52 mg, 0.18 mmol) and DDQ (48 mg, 0.21 mmol) in toluene (10 mL) were heated under reflux for 16 h using anhydrous conditions. The reaction mixture was diluted with EtOAc, filtered, and concentrated under vacuum. Purification of the residue by flash column chromatography (20% EtOAc:hexane) afforded the title product as a yellow solid (22 mg, 43%): mp 216° C. (dec). Anal. RP-HPLC: tR 15.1 min (0-60% MeCN, purity 100%). 1H-NMR (DMSO-d6): δ 10.11 (s, 1H, NH), 9.38 (s, 1H, Py-H), 7.98 (d, 2H, J 7.7, Ph-H), 7.93 (d, 1H, J 8.7, CH), 7.84 (d, 1H, J 8.7, CH), 7.36 (t, 2H, J7.7, Ph-H), 7.02 (t, 1H, J 7.7, Ph-H), 2.91 (s, 3H, CH3). MS (ESI+): m/z 293.07 (M+H)+.

Workup

  1. temperatureunder reflux for 16 h
  2. filtrationfiltered
  3. concentrationconcentrated under vacuum
  4. customPurification of the residue by flash column chromatography (20% EtOAc:hexane)

Sources & evidence

ORD record
ord-753bd9f7a1594d8789b9d237ac79ff38
Source dataset
uspto-grants-2009_08
Patent number
US07576091B2

Reaction notes

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