L-Methioninol → N-[[1-[[[4-[2-(4-Methyl-1-piperazinyl)-4-thiazolyl]phenyl]carbonyl]amino]cyclohexyl]carbonyl]-L-methioninol

HRID 1627492Notes

Reaction equation

HRID 1627492 reaction equation
[NH2:1][C@H:2]([CH2:7][OH:8])[CH2:3][CH2:4][S:5][CH3:6].[CH3:9][N:10]1[CH2:15][CH2:14][N:13]([C:16]2[S:17][CH:18]=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([C:27]4[O:31][C:30](=[O:32])[C:29]5([CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]5)[N:28]=4)=[CH:23][CH:22]=3)[N:20]=2)[CH2:12][CH2:11]1>CN(C)C=O>[CH3:9][N:10]1[CH2:15][CH2:14][N:13]([C:16]2[S:17][CH:18]=[C:19]([C:21]3[CH:22]=[CH:23][C:24]([C:27]([NH:28][C:29]4([C:30]([NH:1][C@H:2]([CH2:7][OH:8])[CH2:3][CH2:4][S:5][CH3:6])=[O:32])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]4)=[O:31])=[CH:25][CH:26]=3)[N:20]=2)[CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 2724404L-MethioninolHCID 576728032-[4-[2-(4-Methyl-1-piperazinyl)-4-thiazolyl]phenyl]-3-oxa-1-azaspiro[4.5]dec-1-en-4-one

Product 1

HCID 57672850N-[[1-[[[4-[2-(4-Methyl-1-piperazinyl)-4-thiazolyl]phenyl]carbonyl]amino]cyclohexyl]carbonyl]-L-methioninolYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

100 mg (0.74 mmol) of L-methioninol was added to a solution of 250 mg (0.68 mmol) of 2-[4-[2-(4-methyl-1-piperazinyl)-4-thiazolyl]phenyl]-3-oxa-1-azaspiro[4.5]dec-1-en-4-one in 20 ml of dimethylformamide. After the mixture was stirred at 80° C. for 15 hours, the reaction solution was concentrated under reduced pressure, ethyl acetate was added thereto, and the mixture was successively washed with water, a saturated aqueous sodium hydrogencarbonate solution and saturated brine, followed by drying with anhydrous sodium sulfate. After the solvent was distilled off under reduced pressure, diisopropyl ether was added to the residue to wash the crystal to obtain 319 mg (86%) of the title compound.

Workup

  1. concentrationthe reaction solution was concentrated under reduced pressure, ethyl acetate
  2. additionwas added
  3. washthe mixture was successively washed with water
  4. dry with materialby drying with anhydrous sodium sulfate
  5. distillationAfter the solvent was distilled off under reduced pressure, diisopropyl ether
  6. additionwas added to the residue
  7. washto wash the crystal

Sources & evidence

ORD record
ord-cb274b8fed8b40039813b82d1505ae21
Source dataset
uspto-grants-2014_07
Patent number
US08785631B2

Reaction notes

Loading…