Potassium Phosphate, Tribasic → (2-(2-Amino-3-morpholinoquinolin-6-yl)-3-methylphenyl)(pyrimidin-4-yl)methanone

HRID 1028979

반응식

HRID 1028979 반응식
Br[C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][N:14]=[CH:13][N:12]=1)=[O:10].[O:17]1[CH2:22][CH2:21][N:20]([C:23]2[C:24]([NH2:42])=[N:25][C:26]3[C:31]([CH:32]=2)=[CH:30][C:29](B2OC(C)(C)C(C)(C)O2)=[CH:28][CH:27]=3)[CH2:19][CH2:18]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(CCC)=CC(CCC)=CC=2CCC)CCCCC1>O1CCOCC1.O.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]>[NH2:42][C:24]1[C:23]([N:20]2[CH2:21][CH2:22][O:17][CH2:18][CH2:19]2)=[CH:32][C:31]2[C:26](=[CH:27][CH:28]=[C:29]([C:2]3[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=3[C:9]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][N:12]=3)=[O:10])[CH:30]=2)[N:25]=1

참가 물질

7

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 21081571Dicyclohexyl(2',4',6'-tripropyl-[1,1'-biphenyl]-2-yl)phosphineHCID 67324109(2-Bromo-3-methylphenyl)(pyrimidin-4-yl)methanoneHCID 673479953-Morpholino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2-amine

생성물 1

HCID 53328997(2-(2-Amino-3-morpholinoquinolin-6-yl)-3-methylphenyl)(pyrimidin-4-yl)methanone

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 218864351,4-Dioxane--water (1/1)용매

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온도
140 °C

실험 절차

A mixture of (2-bromo-3-methylphenyl)(pyrimidin-4-yl)methanone (0.10 g, 0.361 mmol), 3-morpholino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2-amine (0.192 g, 0.541 mmol, prepared as in Example 2, Step 1-2), potassium phosphate tribasic (0.149 mL, 1.804 mmol), Pd2dba3 (0.033 g, 0.036 mmol), and 2-(dicyclohexylphosphino)-2′,4′,6′,-tri-1-propyl-1,1′-biphenyl (0.034 g, 0.072 mmol) in dioxane/water (3/1.5 mL) was heated in mw for 12 min at 140° C. The mixture was concentrated and the resulting crude material was chromatographed on silica gel using 0-5% 2M NH3 in MeOH/DCM to afford a brown oil which was further purified by HPLC to afford (2-(2-amino-3-morpholinoquinolin-6-yl)-3-methylphenyl)(pyrimidin-4-yl)methanone as a yellow solid. MS (ESI, pos. ion) m/z: 426 (M+1).

후처리

  1. concentrationThe mixture was concentrated
  2. customthe resulting crude material was chromatographed on silica gel using 0-5% 2M NH3 in MeOH/DCM
  3. customto afford a brown oil which
  4. customwas further purified by HPLC

출처 및 근거

ORD 기록
ord-4e7041f15c084ad68aeabb015aa440ae
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08735384B2

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