1-Pentanol → (3RS)-[1-(6-Methoxy-[1,5]-naphthyridin-4-yl)-piperidin-3-yl]-carbamic acid tert-butyl ester

HRID 1511798Notes

Reaction equation

HRID 1511798 reaction equation
Br[C:2]1[CH:3]=[CH:4][N:5]=[C:6]2[C:11]=1[N:10]=[C:9]([O:12][CH3:13])[CH:8]=[CH:7]2.[C:14]([O:18][C:19](=[O:27])[NH:20][CH:21]1[CH2:26][CH2:25][CH2:24][NH:23][CH2:22]1)([CH3:17])([CH3:16])[CH3:15].C(O)CCCC>>[C:14]([O:18][C:19](=[O:27])[NH:20][CH:21]1[CH2:26][CH2:25][CH2:24][N:23]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[N:10]=3)[N:5]=[CH:4][CH:3]=2)[CH2:22]1)([CH3:17])([CH3:15])[CH3:16]

Participants

4

Reactant 3

HCID 62761-PentanolHCID 42330413-(Boc-amino)piperidineHCID 534216178-Bromo-2-methoxy-1,5-naphthyridine

Product 1

HCID 66954590(3RS)-[1-(6-Methoxy-[1,5]-naphthyridin-4-yl)-piperidin-3-yl]-carbamic acid tert-butyl ester

Procedure

According to procedure F and starting from 8-bromo-2-methoxy-[1,5]naphthyridine and (RS)-piperidin-3-yl-carbamic acid tert-butyl ester (commercial) and using 1-pentanol instead of NMP as reaction solvent, the title compound was isolated as an orange oil (2.44 g, 68%).

Workup

  1. customas reaction solvent

Sources & evidence

ORD record
ord-39a34abe91294982a7269e1a8a35ea68
Source dataset
uspto-grants-2012_07
Patent number
US08217029B2

Reaction notes

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