4-Methylmorpholine → HCID 44132729, compound

HRID 1916267Notes

Reaction equation

HRID 1916267 reaction equation
[C:1]1(=[O:8])[CH2:6][CH2:5][CH2:4][C:3](=O)[CH2:2]1.[OH:9][CH2:10][CH2:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1.[C:21]([CH2:23][C:24](=[S:26])[NH2:25])#[N:22].CN1CCOCC1.Cl[CH2:35][C:36]1[N:37]=[C:38]([C:41]2[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][CH:42]=2)[S:39][CH:40]=1>C(O)C.O.ClCCl>[Cl:47][C:44]1[CH:43]=[CH:42][C:41]([C:38]2[S:39][CH:40]=[C:36]([CH2:35][S:26][C:24]3[C:23]([C:21]#[N:22])=[C:17]([C:16]4[CH:19]=[CH:20][C:13]([O:12][CH2:11][CH2:10][OH:9])=[CH:14][CH:15]=4)[C:2]4[C:1](=[O:8])[CH2:6][CH2:5][CH2:4][C:3]=4[N:25]=3)[N:37]=2)=[CH:46][CH:45]=1

Participants

9

Reactant 5

HCID 79724-MethylmorpholineHCID 104341,3-CyclohexanedioneHCID 89178Benzaldehyde, 4-(2-hydroxyethoxy)-HCID 6102974-(Chloromethyl)-2-(4-chlorophenyl)-1,3-thiazoleHCID 14162772-Cyanoethanethioamide

Product 1

HCID 44132729HCID 44132729, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

100 mg (0.874 mmol) of 1,3-cyclohexanedione, 150 mg (0.874 mmol) of 4-(hydroxyethoxy)benzaldehyde and 92 mg (0.874 mmol) of 2-cyanoethanethioamide were initially charged in 2.9 ml of ethanol and stirred with 179 mg (1.748 mmol) of N-methylmorpholine at RT overnight. 213 mg (0.874 mmol) of 4-(chloromethyl)-2-(4-chlorophenyl)-1,3-thiazole were then added, and the mixture was stirred at RT for a further 2.5 hours. The reaction mixture was diluted with water and dichloromethane, the two phase were separated and the aqueous phase was extracted four times with dichloromethane. The combined organic phases were washed in each case once with 0.5 N hydrochloric acid and saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The crude product was purified by preparative HPLC [Chromasil, water/acetonitrile+0.15% hydrochloric acid].

Workup

  1. customthe two phase were separated
  2. extractionthe aqueous phase was extracted four times with dichloromethane
  3. washThe combined organic phases were washed in each case once with 0.5 N hydrochloric acid and saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by preparative HPLC [Chromasil, water/acetonitrile+0.15% hydrochloric acid]

Sources & evidence

ORD record
ord-9f8bc1feb48d4e20adf2f9eba1023217
Source dataset
uspto-grants-2013_12
Patent number
US08618119B2

Reaction notes

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