Acetic Acid → 4-methoxy-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

HRID 80771노트

반응식

HRID 80771 반응식
C([N:8]1[CH2:39][CH2:38][C:11]2[N:12]=[C:13]([C:18]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:19]=3[C:20]([CH3:37])=[CH:21][N:22]4[S:27]([C:30]3[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=3)(=[O:29])=[O:28])[N:14]=[C:15]([O:16][CH3:17])[C:10]=2[CH2:9]1)C1C=CC=CC=1.O.C(O)(=O)C>C1COCC1.C(OCC)(=O)C.C([O-])(O)=O.[Na+].[OH-].[OH-].[Pd+2].[C]>[CH3:17][O:16][C:15]1[C:10]2[CH2:9][NH:8][CH2:39][CH2:38][C:11]=2[N:12]=[C:13]([C:18]2[CH:26]=[CH:25][CH:24]=[C:23]3[C:19]=2[C:20]([CH3:37])=[CH:21][N:22]3[S:27]([C:30]2[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=2)(=[O:29])=[O:28])[N:14]=1

참가 물질

8

반응물 3

HCID 176Acetic AcidHCID 962WaterHCID 712405256-benzyl-4-methoxy-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

생성물 1

HCID 712404804-methoxy-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

시약·촉매·용매 4

HCID 178502593HCID 178502593, 화합물촉매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매HCID 516892Sodium Bicarbonate용매

실험 절차

To a solution of 6-benzyl-4-methoxy-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (1.1 g, 2.0 mmol) in THF (15 mL) was added water (3.75 mL) and acetic acid (0.34 mL, 5.9 mmol), then 20 mol % Pd(OH)2/carbon (50% wet) (0.86 g, 0.61 mmol) was added. The reaction mixture was placed under an atmosphere of hydrogen gas via balloon. After 1.5 hours the mixture was diluted with ethyl acetate and neutralized with saturated aqueous NaHCO3. The mixture was then filtered through a pad of Celite®. The eluent was then further diluted with ethyl acetate and brine and the layers were separated. The organic layer was dried over Na2SO4, filtered, and concentrated. The resulting residue was purified by silica gel flash chromatography (0-20% MeOH/DCM) to provide 4-methoxy-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.91 (d, J=1.0 Hz, 3 H) 2.32 (s, 3 H) 2.68 (t, J=5.6 Hz, 2 H) 3.00 (t, J=5.7 Hz, 2 H) 3.72 (s, 2H) 3.92 (s, 3 H) 7.30-7.48 (m, 4 H) 7.65 (d, J=1.0 Hz, 1 H) 7.85 (d, J=8.3 Hz, 2 H) 8.04 (dd, J=7.3, 2.0 Hz, 1 H). MS (ESI+) m/z 449.2 (M+H)+.

후처리

  1. filtrationThe mixture was then filtered through a pad of Celite®
  2. additionThe eluent was then further diluted with ethyl acetate and brine
  3. customthe layers were separated
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by silica gel flash chromatography (0-20% MeOH/DCM)

출처 및 근거

ORD 기록
ord-26906e031b7941958b3fd020eec999b9
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846656B2

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