Methanol → HCID 86635315, compound

HRID 656907Notes

Reaction equation

HRID 656907 reaction equation
[CH2:1]([C:3]1[C:4]([F:17])=[CH:5][N:6]=[C:7]2[C:12]=1[N:11]([CH2:13][CH:14]=O)[C:10](=[O:16])[CH:9]=[CH:8]2)[CH3:2].[NH:18]1[CH2:23][CH2:22][CH:21]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:20][CH2:19]1.CO.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)(Cl)Cl>[CH2:1]([C:3]1[C:4]([F:17])=[CH:5][N:6]=[C:7]2[C:12]=1[N:11]([CH2:13][CH2:14][N:18]1[CH2:19][CH2:20][CH:21]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:29])([CH3:28])[CH3:30])[CH2:22][CH2:23]1)[C:10](=[O:16])[CH:9]=[CH:8]2)[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 7238334-(N-Boc-amino)piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 86635314(8-Ethyl-7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)acetaldehyde

Product 1

HCID 86635315HCID 86635315, compoundYield 77.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

(8-Ethyl-7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)acetaldehyde (0.168 g, 0.718 mmol) and 1,1-dimethylethyl 4-piperidinylcarbamate (0.172 g, 0.860 mmol) was dissolved in CHCl3 (6 ml) and MeOH (0.6 ml) at rt under argon, whereupon NaBH(OAc)3 (0.497 g, 2.34 mmol) was added, after which it was stirred for 3 h. The reaction was then purified by chromatography on silica gel using a 0-20% MeOH in EtOAc gradient to give the title compound as a yellow oil (0.234 g, 72%).

Workup

  1. customThe reaction was then purified by chromatography on silica gel using a 0-20% MeOH in EtOAc gradient

Sources & evidence

ORD record
ord-eee53b1a30c64937b84460dfa5c32574
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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