Tetrahydrofuran → 1-(4-Methoxy-phenyl)-6-(2'-methylaminomethyl-biphenyl-4-yl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c)pyridine-3-carboxylic acid ethyl ester

HRID 497432노트

반응식

HRID 497432 반응식
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][C:18]3[C:21]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[N:22][N:23]([C:24]4[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=4)[C:17]=3[C:16]2=[O:37])=[CH:11][CH:10]=1)=O.Cl.CN.C1COCC1.[C:46]([BH3-])#[N:47].[Na+]>CO.CCOC(C)=O.[Cl-].[Zn+2].[Cl-]>[CH3:31][O:30][C:27]1[CH:26]=[CH:25][C:24]([N:23]2[C:17]3[C:16](=[O:37])[N:15]([C:12]4[CH:13]=[CH:14][C:9]([C:4]5[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=5[CH2:1][NH:47][CH3:46])=[CH:10][CH:11]=4)[CH2:20][CH2:19][C:18]=3[C:21]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[N:22]2)=[CH:29][CH:28]=1

참가 물질

8

반응물 4

HCID 8028TetrahydrofuranHCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochlorideHCID 223185346-(2'-Formyl-biphenyl-4-yl)-1-(4-methoxy-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester

생성물 1

HCID 223185241-(4-Methoxy-phenyl)-6-(2'-methylaminomethyl-biphenyl-4-yl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c)pyridine-3-carboxylic acid ethyl ester수율 102.1%

시약·촉매·용매 3

HCID 3007855Zincchloride촉매HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

Ethyl 6-(2′-formyl-1,1′-biphenyl-4-yl)-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate (485 mg, 0.98 mmol) and methylamine hydrochloride (135 mg, 2 mmol) were added together in 10 mL of 1:1 MeOH:THF and stirred at room temperature for 15 minutes. Zinc chloride (0.5 M in THF, 1 mL, 0.5 mmol) and Sodium cyanoborohydride (63 mg, 1 mmol) were then added and the mixture was stirred at room temperature for 18 hours. The mixture was diluted with EtOAc and washed with H2O, brine, dried over MgSO4, and concentrated to afford 511 mg of desired product (100%). MS (ES+): 511.4, (M+H)+. 1HNMR (CDCl3) δ 7.50-7.41 (m, 3H), 7.39-7.22 (m, 7H), 6.92 (d, 2H), 4.47 (q, 2H), 4.20 (t, 2H), 3.86 (s, 2H), 3.80 (s, 3H) 3.37 (t, 2H), 1.44 (t, 3H) ppm.

후처리

  1. washwashed with H2O, brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-5b6d415081334173a9410110fd8432ae
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06949550B2

반응 노트

불러오는 중…