2-Morpholinoethylamine → HCID 86588190, compound

HRID 1182212Notes

Reaction equation

HRID 1182212 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.[Li]CCCC.C([O:17][C:18]([C:20]1[N:21]=[N:22][S:23][C:24]=1[NH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=O)C>C1COCC1.C1CCCCC1>[N:4]1([CH2:3][CH2:2][NH:1][C:18]([C:20]2[N:21]=[N:22][S:23][C:24]=2[NH:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[O:17])[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1

Participants

6

Reactant 3

HCID 4082852-MorpholinoethylamineHCID 1499213HCID 1499213, compoundHCID 178418339Butyllithium

Product 1

HCID 86588190HCID 86588190, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8078CyclohexaneSolvent

Procedure

To a solution of N-aminoethylmorpholine (228 mg, 10 mmole) in 2 mL anhydrous THF at −40° C. was added 0.8 mL of 2 M n-BuLi solution in cyclohexane. Some white solid was precipitated instantly. The suspension was stirred for about a half an hour. When the bath temperature reached −10° C., a solution of 5-phenylamino-[1,2,3]thiadiazole-4-carboxylic acid ethyl ester (60 mg, 0.24 mmole) in anhydrous THF was added to the mixture. After it was stirred at room temperature for an hour, the reaction was quenched with saturated NH4Cl solution. The solution was extracted with EtOAc and residue obtained after the removal of EtOAc was purified by preparative TLC (silica gel, CH2Cl2:MeOH=15:1). The title compound was isolated as a white powder in 60% yield (48 mg). 1H NMR (ppm, in CDCl3): 10.91 (br. s, 1H), 7.77 (br. s, 1H), 7.00-7.60 (m, 5H), 3.70 (m, 4H), 2.60 (m, 4H).

Workup

  1. customSome white solid was precipitated instantly
  2. customreached −10° C.
  3. stirringAfter it was stirred at room temperature for an hour
  4. customthe reaction was quenched with saturated NH4Cl solution
  5. extractionThe solution was extracted with EtOAc and residue
  6. customobtained
  7. customafter the removal of EtOAc
  8. customwas purified by preparative TLC (silica gel, CH2Cl2:MeOH=15:1)

Sources & evidence

ORD record
ord-0612473642a34ec799a3e9c0e45b053b
Source dataset
uspto-grants-2007_10
Patent number
US07288556B2

Reaction notes

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