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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
ノート
印刷プレビュー

反応式

HRID 1668973 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 9811564
Bis(dibenzylideneacetone)palladium
触媒
HCID 1140Toluene溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
150 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f2a297746a6e4b2cac20743bf1799ce7
出典データセット
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07989461B2

反応ノート

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