4-Methylmorpholine → HCID 67295742, compound

HRID 215909Notes

Reaction equation

HRID 215909 reaction equation
[Cl:1][C:2]1[CH:13]=[C:12]([F:14])[C:11]([N:15]2[C:20](=[O:21])[CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[N:17]([CH3:26])[C:16]2=[O:27])=[CH:10][C:3]=1[O:4][CH:5]([CH3:9])[C:6](O)=[O:7].Cl.[CH3:29][O:30][C:31](=[O:35])[CH2:32][CH2:33][NH2:34].CN1CCOCC1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>ClCCl>[CH3:29][O:30][C:31](=[O:35])[CH2:32][CH2:33][NH:34][C:6](=[O:7])[CH:5]([O:4][C:3]1[CH:10]=[C:11]([N:15]2[C:20](=[O:21])[CH:19]=[C:18]([C:22]([F:23])([F:25])[F:24])[N:17]([CH3:26])[C:16]2=[O:27])[C:12]([F:14])=[CH:13][C:2]=1[Cl:1])[CH3:9]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 18517388HCID 18517388, compound

Product 1

HCID 67295742HCID 67295742, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[2-Chloro-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1(2H)-pyrimidinyl)-4-fluorophenoxy]propionic acid (20 g) and β-alanine methyl ester hydrochloride (8.2 g) were dissolved in dichloromethane (200 mL). After slowly adding 4-methylmorpholine (14.8 g) dropwise to the reaction mixture, stirring was performed for 1 hour. After adding (benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (18.5 g) for 30 minutes, the reaction mixture was stirred at room temperature for 1.5 hours. The reaction mixture was washed with water, dried with magnesium sulfate and concentrated. The concentrate was purified by silica gel column chromatography to give the target compound (24 g) including a trace amount of impurities, which was recrystallized twice using a mixture solvent of ethyl acetate and hexane to give the target compound (18.2 g).

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialdried with magnesium sulfate
  3. concentrationconcentrated
  4. customThe concentrate was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d14a14937902481ba6575a2bced81299
Source dataset
uspto-grants-2012_06
Patent number
US08193198B2

Reaction notes

Loading…