2-Pyrrolidone → HCID 58967539, compound

HRID 909342Notes

Reaction equation

[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][O:21][CH2:22][CH3:23])[N:14]([CH2:15][C:16]([CH3:19])([OH:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6](Br)=[CH:5][C:4]=2[N:3]=1.[O:25]1[CH2:29][CH2:28][NH:27][C:26]1=[O:30].BrC1C=CC2C3N(CCCOC(C)C)C(COCC)=NC=3C(N)=NC=2C=1.N1CCCC1=O>>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][O:21][CH2:22][CH3:23])[N:14]([CH2:15][C:16]([OH:18])([CH3:19])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([N:27]3[CH2:28][CH2:29][O:25][C:26]3=[O:30])=[CH:5][C:4]=2[N:3]=1

Participants

Reactant 4

HCID 120252-Pyrrolidone

HCID 739492-Oxazolidinone

HCID 219842117-bromo-2-ethoxymethyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine

HCID 673820847-Bromo-2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinolin-4-ylamine

Product 1

HCID 58967539HCID 58967539, compound

Procedure

The general method described in Part E of Example 1 was followed using 1-(4-amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol and 2-oxazolidinone as reactants in lieu of 7-bromo-2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinolin-4-amine and 2-pyrrolidinone. The product, 3-[4-amino-2-ethoxymethyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]oxazolidin-2-one, was isolated as a flocculent white solid, mp >250° C.

Sources & evidence

ORD record: ord-510f1271f87e476b8a1ceefa7d147f59
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017779B2

Reaction notes

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