2-Morpholinoethylamine → HCID 86588190, 화합물

HRID 1182212노트

반응식

HRID 1182212 반응식
[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

참가 물질

6

반응물 3

HCID 4082852-MorpholinoethylamineHCID 1499213HCID 1499213, 화합물HCID 178418339Butyllithium

생성물 1

HCID 86588190HCID 86588190, 화합물수율 60%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8078Cyclohexane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-0612473642a34ec799a3e9c0e45b053b
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07288556B2

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