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3-(Trifluoromethyl)aniline → N-methyl-6-(6-methyl-3-(3-(trifluoromethyl)phenylamino)benzo[d]isothiazol-7-yl)quinazolin-2-amine

HRID 1668973
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HRID 1668973 반응식
[NH2:1][C:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH3:23])=[C:10]([C:11]3[CH:12]=[C:13]4[C:18](=[CH:19][CH:20]=3)[N:17]=[C:16]([NH:21][CH3:22])[N:15]=[CH:14]4)[C:5]=2[S:4][N:3]=1.[F:24][C:25]([F:34])([F:33])[C:26]1[CH:27]=[C:28](N)[CH:29]=[CH:30][CH:31]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.CC(C)([O-])C.[Na+]>C(OCC)(=O)C.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>[CH3:22][NH:21][C:16]1[N:15]=[CH:14][C:13]2[C:18](=[CH:19][CH:20]=[C:11]([C:10]3[C:5]4[S:4][N:3]=[C:2]([NH:1][C:30]5[CH:29]=[CH:28][CH:27]=[C:26]([C:25]([F:34])([F:33])[F:24])[CH:31]=5)[C:6]=4[CH:7]=[CH:8][C:9]=3[CH3:23])[CH:12]=2)[N:17]=1
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참가 물질

8

반응물 4

HCID 73753-(Trifluoromethyl)anilineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23676156Sodium t-butoxideHCID 58942254HCID 58942254, 화합물

생성물 1

HCID 67341583N-methyl-6-(6-methyl-3-(3-(trifluoromethyl)phenylamino)benzo[d]isothiazol-7-yl)quinazolin-2-amine

시약·촉매·용매 3

HCID 9811564
Bis(dibenzylideneacetone)palladium
촉매
HCID 1140Toluene용매
HCID 8857Ethyl Acetate용매

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온도
150 °C

실험 절차

6-(3-Amino-6-methylbenzo[d]isothiazol-7-yl)-N-methylquinazolin-2-amine (0.100 g, 0.31 mmol), 3-(trifluoromethyl)benzenamine (0.060 g, 0.37 mmol), tris(dibenzylideneacetone)dipalladium (o) (0.0085 g, 0.0093 mmol), X-phos (0.0089 g, 0.019 mmol) and sodium t-butoxide (0.042 g, 0.44 mmol) were all placed in a clear microwave vial along with 4 ml of toluene. The vial was capped and heated in a Personal Chemistry SmithSynthesizer to 150° C. for 10 minutes. The reaction was diluted with ethyl acetate and the organic layer was washed (2×) with an aqueous saturated solution of sodium bicarbonate, then with water and then brine. The organic layer was then dried with sodium sulfate and purified by column chromatography on silica gel using a gradient of 40-80% EtOAc in hexanes to give N-methyl-6-(6-methyl-3-(3-(trifluoromethyl)phenylamino)benzo[d]isothiazol-7-yl)quinazolin-2-amine as yellow solid. MS (M+H)+ 466.

후처리

  1. customThe vial was capped
  2. washthe organic layer was washed (2×) with an aqueous saturated solution of sodium bicarbonate
  3. dry with materialThe organic layer was then dried with sodium sulfate
  4. custompurified by column chromatography on silica gel using a gradient of 40-80% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-f2a297746a6e4b2cac20743bf1799ce7
출처 데이터셋
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07989461B2

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