Potassium Phosphate, Tribasic → 6-(2-([1,2,4]Triazolo[4,3-a]pyridin-3-yl)-6-methylphenyl)-3-morpholinoquinolin-2-amine

HRID 1028975

반응식

HRID 1028975 반응식
Br[C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[N:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]2=[N:11][N:10]=1.[O:18]1[CH2:23][CH2:22][N:21]([C:24]2[C:25]([NH2:43])=[N:26][C:27]3[C:32]([CH:33]=2)=[CH:31][C:30](B2OC(C)(C)C(C)(C)O2)=[CH:29][CH:28]=3)[CH2:20][CH2:19]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(CCC)=CC(CCC)=CC=2CCC)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>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]>[N:11]1[N:10]=[C:9]([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([CH3:8])[C:2]=2[C:30]2[CH:31]=[C:32]3[C:27](=[CH:28][CH:29]=2)[N:26]=[C:25]([NH2:43])[C:24]([N:21]2[CH2:20][CH2:19][O:18][CH2:23][CH2:22]2)=[CH:33]3)[N:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=12

참가 물질

6

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 21081571Dicyclohexyl(2',4',6'-tripropyl-[1,1'-biphenyl]-2-yl)phosphineHCID 673249633-(2-Bromo-3-methylphenyl)-[1,2,4]triazolo[4,3-a]pyridineHCID 673479953-Morpholino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2-amine

생성물 1

HCID 533289966-(2-([1,2,4]Triazolo[4,3-a]pyridin-3-yl)-6-methylphenyl)-3-morpholinoquinolin-2-amine

시약·촉매·용매 1

HCID 9811564Bis(dibenzylideneacetone)palladium촉매

반응 조건

온도
140 °C

실험 절차

A mixture of 3-(2-bromo-3-methylphenyl)-[1,2,4]triazolo[4,3-a]pyridine (0.32 g, 1.111 mmol), 3-morpholino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2-amine (0.17 g, 0.479 mmol, prepared as in Example 2, Step 1-2), 2-(dicyclohexylphosphino)-2′,4′,6′,-tri-1-propyl-1,1′-biphenyl (0.046 g, 0.096 mmol), potassium phosphate, anhydrous (0.198 mL, 2.393 mmol), and Pd2(dba)3 (0.044 g, 0.048 mmol) was purged with N2 followed by the addition of degassed dioxane (2 mL) and water (1.0 mL). The resulting mixture was heated in microwave at 140° C. for 12 min. The reaction was filtered, concentrated, and the resulting crude material was chromatographed on silica gel using gradient 2:1 hexanes/EtOAc and 0-5% 2M NH3 in MeOH/DCM to afford a light yellow solid. It was repurified by HPLC to afford 6-(2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)-6-methylphenyl)-3-morpholinoquinolin-2-amine as a white solid. MS (ESI, pos. ion) m/z: 437 (M+1).

후처리

  1. customwas purged with N2
  2. additionfollowed by the addition of degassed dioxane (2 mL) and water (1.0 mL)
  3. filtrationThe reaction was filtered
  4. concentrationconcentrated
  5. customthe resulting crude material was chromatographed on silica gel using gradient 2:1 hexanes/EtOAc and 0-5% 2M NH3 in MeOH/DCM
  6. customto afford a light yellow solid
  7. customIt was repurified by HPLC

출처 및 근거

ORD 기록
ord-e305a56c6df94473ad2eec06d29f82b6
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08735384B2

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