Diethylamine → HCID 58931308, compound

HRID 388059Notes

Reaction equation

HRID 388059 reaction equation
CC1C=CC(S(O[CH2:12][C@H:13]2[CH2:15][O:14]2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].[CH2:22]([NH:24][C:25]([C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][C:36]=1[OH:37])[N:33]=[CH:32][CH:31]=[C:30]2[O:38][C:39]1[CH:44]=[CH:43][C:42]([NH:45][C:46]([NH:48][CH3:49])=[O:47])=[C:41]([Cl:50])[CH:40]=1)=[O:26])[CH3:23].[CH2:51]([NH:53][CH2:54][CH3:55])[CH3:52]>O.C(OCC)(=O)C.O1CCCC1.CN(C)C=O>[CH2:22]([NH:24][C:25]([C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][C:36]=1[O:37][CH2:15][C@H:13]([OH:14])[CH2:12][N:53]([CH2:54][CH3:55])[CH2:51][CH3:52])[N:33]=[CH:32][CH:31]=[C:30]2[O:38][C:39]1[CH:44]=[CH:43][C:42]([NH:45][C:46]([NH:48][CH3:49])=[O:47])=[C:41]([Cl:50])[CH:40]=1)=[O:26])[CH3:23]

Participants

8

Reactant 4

HCID 8021DiethylamineHCID 11430Potassium CarbonateHCID 154187Glycidyl tosylate, (R)-HCID 135829396HCID 135829396, compound

Product 1

HCID 58931308HCID 58931308, compoundYield 49.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 21939870Tetrahydrofuran ethyl acetateSolvent

Conditions

Temperature
60 °C

Procedure

After adding (2R)oxiran-2-ylmethyl 4-methyl-1-benzenesulfonate (66 mg, 0.290 mmol), potassium carbonate (32 mg, 0.231 mmol) and dimethylformamide (2 ml) to N6-ethyl-4-(3-chloro-4-(((methylamino)carbonyl)amino)phenoxy)-7-hydroxy-6-quinolinecarboxamide (80.0 mg, 0.193 mmol), the mixture was stirred at 60° C. for 7 hours. Diethylamine (1 ml) was then added, and the mixture was stirred at 60° C. overnight. The reaction solution was distributed between ethyl acetate-tetrahydrofuran (1:1) and water, and the organic layer was washed with water and saturated saline and then dried over anhydrous sodium sulfate. The solvent was distilled off, the residue was subjected to silica gel column chromatography (eluent-ethyl acetate:methanol=95:5), the fraction containing the target substance was concentrated, and crystals were precipitated from ethyl acetate-hexane (1:1), filtered out and blow-dried to obtain the title compound (51.7 mg, 0.095 mmol, 49.3%) as white crystals.

Workup

  1. stirringthe mixture was stirred at 60° C. overnight
  2. washthe organic layer was washed with water and saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off
  5. additionthe fraction containing the target substance
  6. concentrationwas concentrated
  7. customcrystals were precipitated from ethyl acetate-hexane (1:1)
  8. filtrationfiltered out and
  9. customblow-dried

Sources & evidence

ORD record
ord-765c259fcfd54189b766ce58123d262a
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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