4-Toluenesulfonyl chloride → 6-benzyl-4-methoxy-2-(5-methyl-1-tosyl-1H-indazol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

HRID 80795

반응식

HRID 80795 반응식
[CH2:1]([N:8]1[CH2:29][CH2:28][C:11]2[N:12]=[C:13]([C:18]3[C:26]([CH3:27])=[CH:25][CH:24]=[C:23]4[C:19]=3[CH:20]=[N:21][NH:22]4)[N:14]=[C:15]([O:16][CH3:17])[C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[S:32](Cl)([C:35]1[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=1)(=[O:34])=[O:33].[NH4+].[Cl-]>C1COCC1>[CH2:1]([N:8]1[CH2:29][CH2:28][C:11]2[N:12]=[C:13]([C:18]3[C:26]([CH3:27])=[CH:25][CH:24]=[C:23]4[C:19]=3[CH:20]=[N:21][N:22]4[S:32]([C:35]3[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=3)(=[O:34])=[O:33])[N:14]=[C:15]([O:16][CH3:17])[C:10]=2[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 712404666-benzyl-4-methoxy-2-(5-methyl-1H-indazol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

생성물 1

HCID 712406006-benzyl-4-methoxy-2-(5-methyl-1-tosyl-1H-indazol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

6-Benzyl-4-methoxy-2-(5-methyl-1H-indazol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (2.00 g, 5.19 mmol) was added to a suspension of NaH (60% dispersion in mineral oil, 415 mg, 10.4 mmol) in THF (50 mL) at 0° C. After 20 min, TsCl (1.19 g, 6.23 mmol) was added. The reaction mixture was stirred for 20 min and sat aq NH4Cl solution was added to quench excess base. The resulting mixture was extracted with EtOAc (3×). The combined organics were dried (Na2SO4) and concentrated. The residue was purified by silica gel chromatography (0-100% EtOAc/heptane) to provide 6-benzyl-4-methoxy-2-(5-methyl-1-tosyl-1H-indazol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine. MS (ESI+) m/z 540.2 (M+H)+.

후처리

  1. additionwas added
  2. customto quench excess base
  3. extractionThe resulting mixture was extracted with EtOAc (3×)
  4. dry with materialThe combined organics were dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (0-100% EtOAc/heptane)

출처 및 근거

ORD 기록
ord-e2c84dd44598474ca072f91e0a3b2326
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846656B2

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