2-Pyrrolidone → 3-[4-amino-2-ethoxymethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-7-yl]-1,3-oxazolidin-2-one

HRID 909354Notes

Reaction equation

HRID 909354 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:6]3[N:14]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:13]([CH2:19][O:20][CH2:21][CH3:22])=[N:12][C:7]=3[CH:8]=[N:9][C:10]=2[CH:11]=1.BrC1C=CC2C3N(CCCOC(C)C)C(COCC)=NC=3C=[N:31]C=2C=1.[O:48]1[CH2:52][CH2:51][NH:50][C:49]1=[O:53].N1CCCC1=O>>[NH2:31][C:8]1[C:7]2[N:12]=[C:13]([CH2:19][O:20][CH2:21][CH3:22])[N:14]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:6]=2[C:5]2[N:4]=[CH:3][C:2]([N:50]3[CH2:51][CH2:52][O:48][C:49]3=[O:53])=[CH:11][C:10]=2[N:9]=1

Participants

5

Reactant 4

HCID 120252-PyrrolidoneHCID 739492-OxazolidinoneHCID 670524337-bromo-2-(ethoxymethyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridineHCID 673819647-Bromo-2-ethoxymethyl-1-(isopropoxypropyl)-1H-imidazo[4,5-c]quinoline

Product 1

HCID 589675323-[4-amino-2-ethoxymethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-7-yl]-1,3-oxazolidin-2-one

Procedure

The general methods described in Parts A and B of Example 2 were followed using 7-bromo-2-(ethoxymethyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridine in lieu of 7-bromo-2-(ethoxymethyl)-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinoline and 2-oxazolidinone in lieu of 2-pyrrolidinone. The product, 3-[4-amino-2-ethoxymethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-7-yl]-1,3-oxazolidin-2-one (0.125 g) was isolated as an white solid with yellow tinge, m.p. 174-176.5° C.

Sources & evidence

ORD record
ord-d948f6ee71d042338386efa8dbf1d5d8
Source dataset
uspto-grants-2011_09
Patent number
US08017779B2

Reaction notes

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