1-Methoxy-2-methylbut-3-yn-2-ol → (+/-)-2-Amino-7-(3-hydroxy-4-methoxy-3-methylbut-1-yn-1-yl)-N-methyl-4-oxo-1-(pyridin-2-ylmethyl)-1,4-dihydro-1,8-naphthyridine-3-carboxamide hydrochloride

HRID 1260584Notes

Reaction equation

HRID 1260584 reaction equation
[NH2:1][C:2]1[N:3]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[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:17])[N:5]=2.[CH3:25][O:26][CH2:27][C:28]([CH3:32])([OH:31])[C:29]#[CH:30]>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>[ClH:17].[NH2:1][C:2]1[N:3]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[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:30]#[C:29][C:28]([OH:31])([CH3:32])[CH2:27][O:26][CH3:25])[N:5]=2

Participants

7

Reactant 2

HCID 217064261-Methoxy-2-methylbut-3-yn-2-olHCID 866423382-Amino-7-chloro-N-methyl-4-oxo-1-(pyridin-2-ylmethyl)-1,4-dihydro-1,8-naphthyridine-3-carboxamide

Product 1

HCID 68601249(+/-)-2-Amino-7-(3-hydroxy-4-methoxy-3-methylbut-1-yn-1-yl)-N-methyl-4-oxo-1-(pyridin-2-ylmethyl)-1,4-dihydro-1,8-naphthyridine-3-carboxamide hydrochloride

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 1 g of 2-amino-7-chloro-N-methyl-4-oxo-1-(pyridin-2-ylmethyl)-1,4-dihydro-1,8-naphthyridine-3-carboxamide (2.91 mmol) in a mixture of 20 ml of dimethylformamide and 5.7 ml of triethylamine is placed in an 80 ml microwave tube. This suspension is sparged with argon and then 0.498 g of (±)-1-methoxy-2-methyl-3-butyn-2-ol (4.36 mmol), 0.055 g of CuI (0.29 mmol) and 0.102 g of bis(triphenylphosphine)palladium(II)dichloride (0.15 mmol) are successively added.

Workup

  1. customis placed in an 80 ml microwave tube
  2. customThis suspension is sparged with argon

Sources & evidence

ORD record
ord-bedae703bb9249918fc54e99dd050266
Source dataset
uspto-grants-2013_06
Patent number
US08470847B2

Reaction notes

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