Benzothiazole → HCID 70664862, compound

HRID 1403414Notes

Reaction equation

HRID 1403414 reaction equation
Cl[C:2]1[C:11]([N:12]([CH3:16])[CH:13]([CH3:15])[CH3:14])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:17]([O:19][CH3:20])=[O:18])[CH:8]=2)[N:3]=1.[S:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[N:23]=[CH:22]1.C(O[K])(C)=O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[S:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[N:23]=[C:22]1[C:2]1[C:11]([N:12]([CH3:16])[CH:13]([CH3:15])[CH3:14])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:17]([O:19][CH3:20])=[O:18])[CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 7222BenzothiazoleHCID 86667203Methyl 2-chloro-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylateHCID 178476685HCID 178476685, compound

Product 1

HCID 70664862HCID 70664862, compoundYield 9.4%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
150 °C

Procedure

Into a 10-mL sealed was placed methyl 2-chloro-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylate (400 mg, 1.36 mmol), 1,3-benzothiazole (368 mg, 2.72 mmol), Pd(PPh3)4 (80 mg, 0.06 mmol) and AcOK (272 mg, 2.72 mmol) under nitrogen atmosphere. After stirring 4 h at 150° C., the reaction mixture was purified by silica gel column chromatography eluting with 10% ethyl acetate in petroleum ether to afford methyl 2-(1,3-benzothiazol-2-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylate as a light yellow solid (50 mg, 9.4%).

Workup

  1. customInto a 10-mL sealed
  2. customthe reaction mixture was purified by silica gel column chromatography
  3. washeluting with 10% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-7a29b978fa904d7cae00e6fc5d9ba8f9
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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