2-Morpholinoethylamine → HCID 86588190、化合物

HRID 1793845ノート

反応式

HRID 1793845 の反応式
[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

参加物

6

反応物 3

HCID 4082852-MorpholinoethylamineHCID 1499213HCID 1499213、化合物HCID 178418339Butyllithium

生成物 1

HCID 86588190HCID 86588190、化合物収率 60%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8078Cyclohexane溶媒

実験手順

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, 1 H), 7.77 (br. s, 1 H), 7.00-7.60 (m, 5 H), 3.70 (m, 4 H), 2.60 (m, 4 H).

後処理

  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)

出典と根拠

ORDレコード
ord-a7391323bca048d9bd21a6e2605b2ccb
出典データセット
uspto-grants-2006_04
特許番号
US07022702B2

反応ノート

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