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 497432ノート

反応式

HRID 497432 の反応式
[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

参加物

8

反応物 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

生成物 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 ester収率 102.1%

試薬・触媒・溶媒 3

HCID 3007855Zincchloride触媒HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-5b6d415081334173a9410110fd8432ae
出典データセット
uspto-grants-2005_09
特許番号
US06949550B2

反応ノート

読み込み中…