Water → HCID 86591479, compound

HRID 388060Notes

Reaction equation

HRID 388060 reaction equation
[NH2:1][C:2]1[CH:30]=[CH:29][C:5]([O:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:19][CH2:20][C@H:21]([OH:28])[CH2:22][N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])=[C:14]([C:17]#[N:18])[CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.C1([O:37][C:38](=O)[NH:39][C:40]2[S:41][CH:42]=[CH:43][N:44]=2)C=CC=CC=1.O.C(OCC)(=O)C.O1CCCC1>CS(C)=O>[C:17]([C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][C:13]=1[O:19][CH2:20][C@H:21]([OH:28])[CH2:22][N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])[N:10]=[CH:9][CH:8]=[C:7]2[O:6][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:38]([NH:39][C:40]2[S:41][CH:42]=[CH:43][N:44]=2)=[O:37])=[CH:30][CH:29]=1)#[N:18]

Participants

6

Reactant 4

HCID 962WaterHCID 651148phenyl N-(1,3-thiazol-2-yl)carbamateHCID 21939870Tetrahydrofuran ethyl acetateHCID 67201867HCID 67201867, compound

Product 1

HCID 86591479HCID 86591479, compoundYield 54.51%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
85 °C

Procedure

After dissolving 4-(4-aminophenoxy)-6-cyano-7-(((2R)-3-(diethylamino)-2-hydroxypropyl)oxy)quinoline (105 mg, 0.2583 mmol) in dimethylsulfoxide (1 ml), there was added phenyl(thiazol-2-yl)carbamate (60 mg, 0.2712 mmol), and the mixture was heated and stirred at 85° C. for 40 minutes. After cooling to room temperature, water was added to the reaction solution, extraction was performed with ethyl acetate-tetrahydrofuran, and the extract was washed with saturated saline and dried over anhydrous sodium sulfate. Upon distilling off the solvent, the residue was dissolved in acetone and diluted with diethyl ether, and the precipitate was washed with diethyl ether and blow-dried to obtain the title compound (75 mg, 0.1408 mmol, 54.51%) as a light yellow powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureAfter cooling to room temperature
  3. washthe extract was washed with saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationUpon distilling off the solvent
  6. dissolutionthe residue was dissolved in acetone
  7. additiondiluted with diethyl ether
  8. washthe precipitate was washed with diethyl ether
  9. customblow-dried

Sources & evidence

ORD record
ord-2957fc93725e48a399106c1f85afb807
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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