Trifluoroacetic acid → HCID 59594561、化合物

HRID 2262674ノート

反応式

HRID 2262674 の反応式
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1.[CH3:10][CH2:11][C:12](=O)[CH2:13][CH3:14].C(O)(C(F)(F)F)=O>C(OC(C)=O)(C)C>[Cl:9][C:5]1[CH:6]=[C:7]([NH:8][CH:12]([CH2:13][CH3:14])[CH2:11][CH3:10])[C:2]([NH2:1])=[N:3][CH:4]=1

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 7288Ethyl ketoneHCID 12682545-Chloropyridine-2,3-diamine

生成物 1

HCID 59594561HCID 59594561、化合物収率 25%

試薬・触媒・溶媒 1

HCID 7915Isopropyl Acetate溶媒

実験手順

To a solution of 2,3-diamino-5-chloropyridine (7.0 g, 48.6 mmol, 1.0 equiv) and 3-pentanone (6.16 mL, 58.3 mmol, 1.2 equiv) in iPrOAc (100 mL) was added TFA (7.2 mL, 97.2 mmol, 2.0 equiv) by syringe. After stirring for 10 min, NaHB(OAc)3 (20 g, 97.2 mmol, 2.0 equiv) was added as a solid in several portions over ˜5 min. The reaction was allowed to stir overnight. The reaction mixture was then washed with satd. aq. NaHCO3 and brine, and the resulting organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Purification by silica gel MPLC (10%-40% EtOAc/Hexanes) provided 5-chloro-N3-(pentan-3-yl)pyridine-2,3-diamine as a beige solid (2.6 g, 25%). m/z=214.1 [M+H]+

後処理

  1. stirringto stir overnight
  2. washThe reaction mixture was then washed with satd
  3. dry with materialaq. NaHCO3 and brine, and the resulting organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel MPLC (10%-40% EtOAc/Hexanes)

出典と根拠

ORDレコード
ord-4ce7b64c968c45f990c1644bce7b8dc7
出典データセット
uspto-grants-2010_12
特許番号
US07851484B2

反応ノート

読み込み中…