Sodium Hydroxide → HCID 71258375, compound

HRID 1506261Notes

Reaction equation

HRID 1506261 reaction equation
Cl.[CH3:2][C@@H:3]1[CH2:8][CH2:7][NH:6][CH2:5][C@@H:4]1[N:9]1[C:18]2[C:13](=[CH:14][N:15]=[C:16]3[NH:21][CH:20]=[CH:19][C:17]3=2)[C:12](=[O:22])[CH:11]=[CH:10]1.[F:23][C:24]1[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:25]=1[CH:26]=O.B.N1C=CC=CC=1C.C(=O)([O-])O.[Na+].[OH-].[Na+]>CO.C(O)(=O)C>[F:23][C:24]1[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:25]=1[CH2:26][N:6]1[CH2:7][CH2:8][C@@H:3]([CH3:2])[C@@H:4]([N:9]2[C:18]3[C:13](=[CH:14][N:15]=[C:16]4[NH:21][CH:20]=[CH:19][C:17]4=3)[C:12](=[O:22])[CH:11]=[CH:10]2)[CH2:5]1

Participants

8

Reactant 5

HCID 14798Sodium HydroxideHCID 1376642,3-DifluorobenzaldehydeHCID 516892Sodium BicarbonateHCID 16217944Borane;2-methylpyridineHCID 118588249HCID 118588249, compound

Product 1

HCID 71258375HCID 71258375, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

rac-1-[(3R,4R)-4-methylpiperidin-3-yl]-1H-pyrrolo[2,3-h][1,6]naphthyridin-4(7H)-one hydrochloride (18 mg, 0.057 mmol) and 2,3-difluorobenzaldehyde (10 mg, 0.070 mmol) in a mixture of methanol (1 mL)/acetic acid (1 mL) was stirred with 2-picoline borane (10 mg, 0.094 mmol) at room temperature for one day. After addition of saturated aqueous sodium hydrogen carbonate and 1 M aqueous sodium hydroxide, the reaction mixture was extracted with chloroform, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel thin layer chromatography (chloroform/methanol=20/1 (v/v)) to give rac-1-[(3R,4R)-1-(2,3-difluorobenzyl)-4-methylpiperidin-3-yl]-1H-pyrrolo[2,3-h][1,6]naphthyridin-4(7H)-one (less polar fraction: 6.1 mg, yield 26%) as a pale yellow solid and rac-1-[(3R,4R)-1,4-dimethylpiperidin-3-yl]-1H-pyrrolo[2,3-h][1,6]naphthyridin-4(7H)-one (more polar fraction: 5.9 mg, yield 35%) as a colorless oil.

Workup

  1. extractionthe reaction mixture was extracted with chloroform
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel thin layer chromatography (chloroform/methanol=20/1 (v/v))

Sources & evidence

ORD record
ord-b7b783d7c4a14cb681a1222acbe37801
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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