2-Methoxyethyl isothiocyanate → 7-(3,5-dimethyl-4-isoxazolyl)-1-[1-methyl-2-(methyloxy)ethyl]-8-(methyloxy)-N-[2-(methyloxy)ethyl]-1H-imidazo[4,5-c]quinolin-2-amine

HRID 82006Notes

Reaction equation

HRID 82006 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:16]=[C:15]3[C:10]([C:11]([NH:18][CH:19]([CH3:23])[CH2:20][O:21][CH3:22])=[C:12]([NH2:17])[CH:13]=[N:14]3)=[CH:9][C:8]=2[O:24][CH3:25])=[C:5]([CH3:26])[O:4][N:3]=1.[N:27]([CH2:30][CH2:31][O:32][CH3:33])=[C:28]=S>>[CH3:1][C:2]1[C:6]([C:7]2[C:8]([O:24][CH3:25])=[CH:9][C:10]3[C:11]4[N:18]([CH:19]([CH3:23])[CH2:20][O:21][CH3:22])[C:28]([NH:27][CH2:30][CH2:31][O:32][CH3:33])=[N:17][C:12]=4[CH:13]=[N:14][C:15]=3[CH:16]=2)=[C:5]([CH3:26])[O:4][N:3]=1

Participants

3

Reactant 2

HCID 1234752-Methoxyethyl isothiocyanateHCID 709803797-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N4-(1-methoxypropan-2-yl)quinoline-3,4-diamine

Product 1

HCID 665714057-(3,5-dimethyl-4-isoxazolyl)-1-[1-methyl-2-(methyloxy)ethyl]-8-(methyloxy)-N-[2-(methyloxy)ethyl]-1H-imidazo[4,5-c]quinolin-2-amineYield 47%

Procedure

From 7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N4-(1-methoxypropan-2-yl)quinoline-3,4-diamine (for a preparation see Intermediate 19) (70 mg) and 1-isothiocyanato-2-(methyloxy)ethane (50 mg) to give the title compound as beige solid (41 mg, 47%). LCMS (formate) Rt 0.56 min, MH+ 440.

Sources & evidence

ORD record
ord-71daeeffaa01432a9f253fab4e0e811b
Source dataset
uspto-grants-2014_09
Patent number
US08846709B2

Reaction notes

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