Cesium carbonate → 4-[(5-Methoxy[1,3]thiazolo[5,4-b]pyridin-2-yl)amino]-6-quinazolinyl acetate

HRID 81659

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].[C:7]([O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[CH:16][N:15]=[C:14]2Cl)(=[O:9])[CH3:8].[CH3:22][O:23][C:24]1[N:29]=[C:28]2[S:30][C:31]([NH2:33])=[N:32][C:27]2=[CH:26][CH:25]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[C:7]([O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[CH:16][N:15]=[C:14]2[NH:33][C:31]1[S:30][C:28]2[C:27]([N:32]=1)=[CH:26][CH:25]=[C:24]([O:23][CH3:22])[N:29]=2)(=[O:9])[CH3:8]

Participants

Conditions

Temperature: 120 °C

Procedure

Cesium carbonate (880 mg, 2.7 mmol) and 1,1′-binaphthalene-2,2′-diylbis(diphenylphosphine) (168 mg, 0.27 mmol) and tris(dibenzylideneacetone)dipalladium(0) (123 mg, 0.14 mmol) were successively added to a toluene solution (10 ml) of 4-chloro-6-quinazolinyl acetate (300 mg, 1.35 mmol) and 5-methoxy[1,3]thiazolo[5,4-b]pyridine-2-amine (244 mg, 1.35 mmol), and stirred under a nitrogen atmosphere at 120° C. for 2 hours. The reaction solution was cooled to room temperature, filtered, and washed with chloroform and methanol. The obtained filtrate was concentrated under reduced pressure to obtain 4-[(5-methoxy[1,3]thiazolo[5,4-b]pyridin-2-yl)amino]-6-quinazolinyl acetate (196 mg, yield: 40%) as a yellow solid.

Workup

temperatureThe reaction solution was cooled to room temperature
filtrationfiltered
washwashed with chloroform and methanol
concentrationThe obtained filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-132c72bd5ee94a9fbe08b12bdfaecbca
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846700B2

Linked notes

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