Ethyl isothiocyanate → HCID 66571409, compound

HRID 82011Notes

Reaction equation

HRID 82011 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]([C:21]4[CH:22]=[N:23][N:24]([CH3:26])[CH:25]=4)[CH3:20])=[C:12]([NH2:17])[CH:13]=[N:14]3)=[CH:9][C:8]=2[O:27][CH3:28])=[C:5]([CH3:29])[O:4][N:3]=1.[CH2:30]([N:32]=[C:33]=S)[CH3:31]>C(O)C>[CH3:1][C:2]1[C:6]([C:7]2[C:8]([O:27][CH3:28])=[CH:9][C:10]3[C:11]4[N:18]([CH:19]([C:21]5[CH:22]=[N:23][N:24]([CH3:26])[CH:25]=5)[CH3:20])[C:33]([NH:32][CH2:30][CH3:31])=[N:17][C:12]=4[CH:13]=[N:14][C:15]=3[CH:16]=2)=[C:5]([CH3:29])[O:4][N:3]=1

Participants

4

Reactant 2

HCID 10966Ethyl isothiocyanateHCID 70980161HCID 70980161, compound

Product 1

HCID 66571409HCID 66571409, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

7-(3,5-Dimethylisoxazol-4-yl)-6-methoxy-N4-(1-(1-methyl-1H-pyrazol-4-yl)ethyl)quinoline-3,4-diamine (70 mg, 0.178 mmol, for a preparation see intermediate 22) was dissolved in ethanol (5 ml) and ethylisothiocyanate (31.1 mg, 0.357 mmol) was added. The solution was heated at 60° C. for 3 h, then cooled and evaporated in vacuo. The residue was dissolved in THF and heated to 60° C. for 4 h, then evaporated in vacuo and the residue dissolved in DMSO and purified by MDAP (formic method. The product-containing fractions were evaporated in vacuo to give 7-(3,5-dimethylisoxazol-4-yl)-N-ethyl-8-methoxy-1-(1-(1-methyl-1H-pyrazol-4-yl)ethyl)-1H-imidazo[4,5-c]quinolin-2-amine (32 mg, 0.072 mmol, 40.3% yield) as a beige solid. LCMS (formate) Rt 0.71 min, MH+ not found.

Workup

  1. temperaturecooled
  2. customevaporated in vacuo
  3. dissolutionThe residue was dissolved in THF
  4. temperatureheated to 60° C. for 4 h
  5. customevaporated in vacuo
  6. dissolutionthe residue dissolved in DMSO
  7. custompurified by MDAP (formic method
  8. customThe product-containing fractions were evaporated in vacuo

Sources & evidence

ORD record
ord-d37479762d7b444ea6f480f8675a44e7
Source dataset
uspto-grants-2014_09
Patent number
US08846709B2

Reaction notes

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