Dimethylformamide → HCID 58942254, 화합물

HRID 2092330노트

반응식

HRID 2092330 반응식
[CH3:1][NH:2][C:3]1[N:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8](B3OC(C)(C)C(C)(C)O3)[CH:9]=2)[N:4]=1.I[C:23]1[C:31]2[S:30][N:29]=[C:28]([NH2:32])[C:27]=2[CH:26]=[CH:25][C:24]=1[CH3:33].C(=O)([O-])[O-].[Na+].[Na+].CN(C=O)C>O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:32][C:28]1[C:27]2[CH:26]=[CH:25][C:24]([CH3:33])=[C:23]([C:8]3[CH:9]=[C:10]4[C:5](=[CH:6][CH:7]=3)[N:4]=[C:3]([NH:2][CH3:1])[N:12]=[CH:11]4)[C:31]=2[S:30][N:29]=1

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 16086139N-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)quinazolin-2-amineHCID 584664897-Iodo-6-methylbenzo[d]isothiazol-3-amine

생성물 1

HCID 58942254HCID 58942254, 화합물

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매2회

반응 조건

온도
150 °C

실험 절차

N-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinazolin-2-amine (0.42 g, 1.5 mmol), 7-iodo-6-methylbenzo[d]isothiazol-3-amine (0.39 g, 1.3 mmol), dichlorobis(triphenyl-phosphine)palladium (II) (0.047 g, 0.067 mmol) and sodium carbonate (0.14 g, 1.3 mmol) were all placed in a clear microwave vial along with 5 ml of 9:1 DMF:water. The vial was capped and heated in a Personal Chemistry SmithSynthesizer to 150° C. for 10 minutes. The reaction was diluted with water and extracted with EtAOc. 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 50 to 100% EtOAc in hexanes. The clean fractions were triturated with warm ether and the solid collected by suction filtration and dried to give 6-(3-amino-6-methylbenzo[d]isothiazol-7-yl)-N-methylquinazolin-2-amine as a tan solid. MS(M+H)+ 322.

후처리

  1. customThe vial was capped
  2. extractionextracted with EtAOc
  3. washThe organic layer was washed (2×) with an aqueous saturated solution of sodium bicarbonate
  4. dry with materialThe organic layer was then dried with sodium sulfate
  5. custompurified by column chromatography on silica gel using a gradient of 50 to 100% EtOAc in hexanes
  6. customThe clean fractions were triturated with warm ether
  7. filtrationthe solid collected by suction filtration
  8. customdried

출처 및 근거

ORD 기록
ord-3a1149ce03194f9bbaa2c2323e2b0af1
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08440674B2

반응 노트

불러오는 중…