Acetic Acid → 1-{1-[(5-Chlorothiophen-2-yl)methyl]piperidin-4-yl}-7-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-h][1,6]naphthyridin-4(7H)-one

HRID 1506242Notes

Reaction equation

HRID 1506242 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:16]3[C:11](=[CH:12][N:13]=[C:14]4[N:19]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[CH:18]=[CH:17][C:15]4=3)[C:10](=[O:28])[CH:9]=[CH:8]2)[CH2:3][CH2:2]1.[Cl:29][C:30]1[S:34][C:33]([CH:35]=O)=[CH:32][CH:31]=1.B.N1C=CC=CC=1C.C(O)(=O)C>CO>[Cl:29][C:30]1[S:34][C:33]([CH2:35][N:1]2[CH2:6][CH2:5][CH:4]([N:7]3[C:16]4[C:11](=[CH:12][N:13]=[C:14]5[N:19]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:25])([CH3:27])[CH3:26])[CH:18]=[CH:17][C:15]5=4)[C:10](=[O:28])[CH:9]=[CH:8]3)[CH2:3][CH2:2]2)=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 817002-Thiophenecarboxaldehyde, 5-chloro-HCID 16217944Borane;2-methylpyridineHCID 712582261-(Piperidin-4-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-h][1,6]naphthyridin-4(7H)-one

Product 1

HCID 867266401-{1-[(5-Chlorothiophen-2-yl)methyl]piperidin-4-yl}-7-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-h][1,6]naphthyridin-4(7H)-oneYield 75.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(Piperidin-4-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-h][1,6]naphthyridin-4(7H)-one (20 mg, 0.050 mmol) in methanol was stirred with 5-chlorothiophen-2-carbaldehyde (6.3 μL, 0.06 mmol), 2-picoline borane (6.4 mg, 0.06 mmol) and acetic acid (100 μL) for one day. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/methanol=10/1 (v/v)) to give the title compound as a colorless oil (20 mg, yield 75%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (chloroform/methanol=10/1 (v/v))

Sources & evidence

ORD record
ord-81aac1c10a2a465eaf9c320de049c5ee
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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