Phenylacetyl isothiocyanate → 1-[6-(6,7-Dimethoxy-quinolin-4-yloxy)-pyridin-3-yl]-3-phenylacetyl-thiourea

HRID 445453Notes

Reaction equation

HRID 445453 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[N:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1.[C:23]1([CH2:29][C:30]([N:32]=[C:33]=[S:34])=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CCOC(C)=O.CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[N:21]=[CH:20][C:19]([NH:22][C:33]([NH:32][C:30](=[O:31])[CH2:29][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[S:34])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 12454157Phenylacetyl isothiocyanateHCID 229365976-(6,7-Dimethoxyquinolin-4-yloxy)pyridin-3-amine

Product 1

HCID 113404701-[6-(6,7-Dimethoxy-quinolin-4-yloxy)-pyridin-3-yl]-3-phenylacetyl-thioureaYield 298.7%

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

To a round bottom flask equipped with a magnetic stir bar was added 6-(6,7-dimethoxy-quinolin-4-yloxy)-pyridin-3-ylamine (85 mg, 0.0285 mmol, 1.0 eq.), and Phenyl-acetyl isothiocyanate (256 mg, 1.44 mmol, 5.0 eq.) dissolved in EtOAc/MeOH 50:50 (2 mL). The reaction mixture was sittred at room temperature for 12 hours, and the solvent was evaporated via rotary evaporation. Purification was done on Biotage with solvent system 95% EtOAc, 4% TEA and 1% MeOH. The combined pure fractions were concentrated and dried under vacuum overnight to yield 1-[6-(6,7-dimethoxy-quinolin-4-yloxy)-pyridin-3-yl]-3-phenylacetyl-thiourea as a light yellow solid (40.4 mg, 29.7%). 1H NMR (400 MHz, CDCl3): 8.65 (d, 1H), 8.33 (d, 1H), 8.27 (dd, 1H), 7.35 (m, 7H), 7.15 (d, 1H), 6.92 (d, 1H), 4.05 (s, 3H), 3.99 (s, 3H), 3.76 (s, 2H); MS (EI) for C25H22N4O4S: 475 (M+H+).

Workup

  1. customTo a round bottom flask equipped with a magnetic stir bar
  2. customthe solvent was evaporated via rotary evaporation
  3. customPurification
  4. concentrationThe combined pure fractions were concentrated
  5. customdried under vacuum overnight

Sources & evidence

ORD record
ord-2c9c904ea64c405a959a00ec2af407cb
Source dataset
uspto-grants-2013_07
Patent number
US08476298B2

Reaction notes

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