4-Methylmorpholine → HCID 12992635, compound

HRID 353377Notes

Reaction equation

HRID 353377 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=2)[CH2:9][CH2:8]1.ON1C2C=C[CH:30]=[CH:31][C:26]=2N=N1.C[N:33]1CC[O:36][CH2:35][CH2:34]1.Cl.[CH2:40](N=C=NCCCN(C)C)C.[C:51](=[O:54])([O-])[OH:52].[Na+]>CN(C)C=O>[OH:36][C@@H:35]([CH2:34][NH:33][C:17](=[O:18])[C:16]1[CH:20]=[CH:21][C:13]([N:10]2[CH2:9][CH2:8][N:7]([C:2]3[N:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[CH2:12][CH2:11]2)=[CH:14][CH:15]=1)[C:51]([O:52][C:31]([CH3:30])([CH3:26])[CH3:40])=[O:54]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12050482HCID 12050482, compound

Product 1

HCID 12992635HCID 12992635, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Dimethylformamide (5.0 ml) was added to 32.1 mg of 4-{4-(pyrimidin-2-yl)piperazin-1-yl}benzoic acid (WO 99/38849) to prepare a solution, and 24.0 mg of 1-hydroxybenzotriazole and 0.060 ml of N-methylmorpholine were successively added to the solution. A solution of 17.9 mg of intermediate 1 in 5.0 ml of dimethylformamide and 45.6 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride were added in that order to the mixture, and a reaction was allowed to proceed at room temperature for 24 hr. A saturated aqueous sodium hydrogencarbonate solution (100 ml) was added to the reaction solution. The mixture was extracted three times with 100 ml of ethyl acetate, and the ethyl acetate layers were combined. The combined ethyl acetate layers were washed with 100 ml of water, were dried over anhydrous magnesium sulfate, and were then filtered. The filtrated was concentrated under the reduced pressure. The residue was purified by column chromatography on silica gel (57 g, ethyl acetate-methanol=15:1) to give 37.6 mg of the title compound.

Workup

  1. additionwere successively added to the solution
  2. extractionThe mixture was extracted three times with 100 ml of ethyl acetate
  3. washThe combined ethyl acetate layers were washed with 100 ml of water
  4. dry with materialwere dried over anhydrous magnesium sulfate
  5. filtrationwere then filtered
  6. concentrationThe filtrated was concentrated under the reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (57 g, ethyl acetate-methanol=15:1)

Sources & evidence

ORD record
ord-3b743867c8f147e3adce3da338226238
Source dataset
uspto-grants-2004_06
Patent number
US06750219B1

Reaction notes

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