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 497432Notes

Reaction equation

HRID 497432 reaction equation
[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

Participants

8

Reactant 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

Product 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 esterYield 102.1%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-5b6d415081334173a9410110fd8432ae
Source dataset
uspto-grants-2005_09
Patent number
US06949550B2

Reaction notes

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