Hydroxylamine → HCID 178526363、化合物

HRID 1845790ノート

反応式

HRID 1845790 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[C:16]([CH2:17][CH2:18][CH2:19][N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[N:15][O:14][N:13]=2)=O)[CH:5]=[CH:6][C:7]=1[F:8].P(Cl)(Cl)(Cl)(Cl)Cl.[NH2:32][OH:33]>C1C=CC=CC=1.CO>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[C:16]([CH2:17][CH2:18][CH2:19][N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[N:15][O:14][N:13]=2)=[N:32][OH:33])[CH:5]=[CH:6][C:7]=1[F:8]

参加物

6

反応物 3

HCID 787HydroxylamineHCID 24819Phosphorus pentachlorideHCID 58941763N-(3-chloro-4-fluorophenyl)-4-(3-morpholin-4-ylpropyl)-1,2,5-oxadiazole-3-carboxamide

生成物 1

HCID 178526363HCID 178526363、化合物収率 50.2%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 887Methanol溶媒

実験手順

N-(3-Chloro-4-fluorophenyl)-4-(3-morpholin-4-ylpropyl)-1,2,5-oxadiazole-3-carboxamide (10.0 mg, 27 μmol) was suspended in benzene (0.4 mL) under an atmosphere of nitrogen and phosphorus pentachloride (6.2 mg, 29.8 μmol) was added. The solution was heated at reflux for 2.5 h. The volatiles were evaporated in vacuo. The reaction was dissolved in EtOH (0.3 mL) and hydroxylamine (40 μL, 0.7 mmol) (50% solution in water) was added to the reaction. After stirring for 1 h, the reaction solution was diluted with MeOH and purified by preparative LCMS to give the desired product (5.2 mg, 50%). LCMS for C16H20ClFN5O3(M+H)+: m/z=384.1.

後処理

  1. temperatureThe solution was heated
  2. temperatureat reflux for 2.5 h
  3. customThe volatiles were evaporated in vacuo
  4. dissolutionThe reaction was dissolved in EtOH (0.3 mL)
  5. custompurified by preparative LCMS

出典と根拠

ORDレコード
ord-0272e5ff2f7f4a51883797f1838c9550
出典データセット
uspto-grants-2015_02
特許番号
US08951536B2

反応ノート

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