(+/-)-2-Cyclopropyl-1-methoxybut-3-yn-2-ol → (+/-)-2-Amino-7-(3-cyclopropyl-3-hydroxy-4-methoxybut-1-yn-1-yl)-1-ethyl-N-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide

HRID 1260591Notes

Reaction equation

HRID 1260591 reaction equation
[NH2:1][C:2]1[N:3]([CH2:18][CH3:19])[C:4]2[C:9]([C:10](=[O:16])[C:11]=1[C:12]([NH:14][CH3:15])=[O:13])=[CH:8][CH:7]=[C:6](Cl)[N:5]=2.[CH:20]1([C:23]([OH:29])([C:27]#[CH:28])[CH2:24][O:25][CH3:26])[CH2:22][CH2:21]1>CN(C)C=O.C(N(CC)CC)C.[Cu]I.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[NH2:1][C:2]1[N:3]([CH2:18][CH3:19])[C:4]2[C:9]([C:10](=[O:16])[C:11]=1[C:12]([NH:14][CH3:15])=[O:13])=[CH:8][CH:7]=[C:6]([C:28]#[C:27][C:23]([CH:20]1[CH2:22][CH2:21]1)([OH:29])[CH2:24][O:25][CH3:26])[N:5]=2

Participants

7

Reactant 2

HCID 80410057(+/-)-2-Cyclopropyl-1-methoxybut-3-yn-2-olHCID 866423362-Amino-7-chloro-1-ethyl-N-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide

Product 1

HCID 67081342(+/-)-2-Amino-7-(3-cyclopropyl-3-hydroxy-4-methoxybut-1-yn-1-yl)-1-ethyl-N-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A suspension of 0.47 g (1.68 mmol) of 2-amino-7-chloro-1-ethyl-N-methyl-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxamide in a mixture of 8.4 ml of dimethylformamide and 3 ml of triethylamine is placed in a 10 ml microwave tube. This suspension is sparged with argon for 10 minutes and then 0.433 g of (±)-2-cyclopropyl-1-methoxybut-3-yn-2-ol (3.09 mmol), 0.032 g of CuI (0.17 mmol) and 0.059 g of bis(triphenylphosphine) palladium(II)dichloride (0.08 mmol) are successively added.

Workup

  1. customis placed in a 10 ml microwave tube
  2. customThis suspension is sparged with argon for 10 minutes

Sources & evidence

ORD record
ord-b500c8e8fca34205828925bac12eb4eb
Source dataset
uspto-grants-2013_06
Patent number
US08470847B2

Reaction notes

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