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2-Fluorobenzoic acid → N-(4-Chloro-5-(1-(4-chlorophenyl)-4,5-dihydro-5-oxo-1H-1,2,4-triazol-3-yl)-2-fluorobenzyl)-2-fluorobenzamide

HRID 59537
ノート
印刷プレビュー

反応式

HRID 59537 の反応式
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.S(Cl)(Cl)=O.[NH2:15][CH2:16][C:17]1[C:18]([F:37])=[CH:19][C:20]([Cl:36])=[C:21]([C:23]2[NH:24][C:25](=[O:35])[N:26]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=3)[N:27]=2)[CH:22]=1.CCN(C(C)C)C(C)C>C1COCC1.CN(C=O)C>[Cl:36][C:20]1[C:21]([C:23]2[NH:24][C:25](=[O:35])[N:26]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=3)[N:27]=2)=[CH:22][C:17]([CH2:16][NH:15][C:4](=[O:6])[C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=2[F:1])=[C:18]([F:37])[CH:19]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 99352-Fluorobenzoic acidHCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 1366448485-(5-(aminomethyl)-2-chloro-4-fluorophenyl)-2-(4-chlorophenyl)-2H-1,2,4-triazol-3 (4H)-one

生成物 1

HCID 136246041N-(4-Chloro-5-(1-(4-chlorophenyl)-4,5-dihydro-5-oxo-1H-1,2,4-triazol-3-yl)-2-fluorobenzyl)-2-fluorobenzamide収率 9.5%

試薬・触媒・溶媒

2
HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 2-fluoro benzoic acid (0.400 g), thionyl chloride (20 mL) and DMF (cat. amt.) was refluxed for 5 h and excess of solvent was removed under reduced pressure to obtain crude product. The obtained crude product was added to the solution of 5-(5-(aminomethyl)-2-chloro-4-fluorophenyl)-2-(4-chlorophenyl)-2H-1,2,4-triazol-3 (4H)-one (Intermediate-78, 0.250 g) and DIPEA (1.0 mL) in THF (20 mL) and the reaction mass was stirred for 3 h. After completion of reaction, reaction mass was quenched with water and extracted with ethyl acetate. The organic layer was separated, concentrated to afford 0.032 g of the desired product. 1H NMR (300 MHz, DMSO): δ 4.53 (br s, 2H), 7.29 (m, 2H), 7.70 (m, 3H), 7.78 (m, 3H), 7.95 (br s, 2H), 8.94 (br s, 1H), 12.63 (br s, 1H); MS (m/z): 475.39 (M+H)+.

後処理

  1. temperaturewas refluxed for 5 h and excess of solvent
  2. customwas removed under reduced pressure
  3. customto obtain crude product
  4. customThe obtained crude product
  5. customAfter completion of reaction, reaction mass
  6. customwas quenched with water
  7. extractionextracted with ethyl acetate
  8. customThe organic layer was separated
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-aaa69057702d4e17bd5a5c8ee6c701e5
出典データセット
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09439890B2

反応ノート

読み込み中…

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