N,N,2,2-Tetramethylpropane-1,3-diamine → N-(4-(3-(2-(3-(dimethylamino)-2,2-dimethylpropylamino)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)4-phenylphthalazin-1-amine

HRID 227789

반응식

HRID 227789 반응식
CS([C:5]1[N:10]=[C:9]([C:11]2[C:12]([O:17][C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25]4[C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[C:28]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)=[N:27][N:26]=4)=[CH:20][CH:19]=3)=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:8]=[CH:7][N:6]=1)(=O)=O.[CH3:41][N:42]([CH3:49])[CH2:43][C:44]([CH3:48])([CH3:47])[CH2:45][NH2:46]>CS(C)=O>[CH3:41][N:42]([CH3:49])[CH2:43][C:44]([CH3:48])([CH3:47])[CH2:45][NH:46][C:5]1[N:10]=[C:9]([C:11]2[C:12]([O:17][C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25]4[C:40]5[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=5)[C:28]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)=[N:27][N:26]=4)=[CH:20][CH:19]=3)=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:8]=[CH:7][N:6]=1

참가 물질

4

반응물 2

HCID 104477N,N,2,2-Tetramethylpropane-1,3-diamineHCID 66731697HCID 66731697, 화합물

생성물 1

HCID 57756233N-(4-(3-(2-(3-(dimethylamino)-2,2-dimethylpropylamino)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)4-phenylphthalazin-1-amine

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매2회

반응 조건

온도
70 °C

실험 절차

A resealable pressure vial was charged with N-(4-(3-(2-(methylsulfonyl)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)-4-phenylphthalazin-1-amine (100 mg, 0.180 mmol) and N1,N1,2,2-tetramethylpropane-1,3-diamine (0.12 ml, 0.73 mmol) and DMSO (1.2 ml, 0.15 M). The reaction vessel was sealed and the mixture was stirred at 70° C. for 16 hrs. The reaction was cooled to RT and diluted with 3 ml of DMSO. The solution was purified by Gilson reverse phase chromatography (10% to 90% CH3CN/H2O/0.1% TFA). The product-containing fractions were combined, basified by addition of aq. NaHCO3 and extracted with ethyl acetate. The organic portion was dried with Na2SO4, filtered, and concentrated to afford pure N-(4-(3-(2-(3-(dimethylamino)-2,2-dimethylpropylamino)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)4-phenylphthalazin-1-amine as a yellow solid. MS m/z=597 [M+H]+. Calc'd for C36H36N8O: 596.72.

후처리

  1. customThe reaction vessel was sealed
  2. temperatureThe reaction was cooled to RT
  3. customThe solution was purified by Gilson reverse phase chromatography (10% to 90% CH3CN/H2O/0.1% TFA)
  4. additionbasified by addition of aq. NaHCO3
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic portion was dried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-92b68cb256ac4dfea4160fe52c0d1268
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560551B2

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