Sodium hydride → HCID 136492459、化合物

HRID 509054ノート

反応式

HRID 509054 の反応式
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Br[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[NH:20][C:19](=[O:21])[N:18]([C:22]3[CH:23]=[C:24]([CH:33]=[CH:34][C:35]=3[Cl:36])[CH2:25][NH:26][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])[N:17]=2)=[CH:12][CH:11]=1>CN(C=O)C>[Cl:36][C:35]1[CH:34]=[CH:33][C:24]([CH2:25][NH:26][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:23][C:22]=1[N:18]1[C:19](=[O:21])[NH:20][C:16]([C:13]2[CH:12]=[CH:11][C:10]([CH2:9][N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:15][CH:14]=2)=[N:17]1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 31268PyrrolidineHCID 136644856N-(3-(3-(4-(bromomethyl)phenyl)-4,5-dihydro-5-oxo-1,2,4-triazol-1-yl)-4-chlorobenzyl)pivalamide

生成物 1

HCID 136492459HCID 136492459、化合物収率 10.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a cold solution of pyrrolidine (0.060 g, 0.830 mmol) in DMF was added NaH (0.034 g, 0.830 mmol) at 0° C. and stirred the reaction mass for 1 h. Then solution of N-(3-(3-(4-(bromomethyl)phenyl)-4,5-dihydro-5-oxo-1,2,4-triazol-1-yl)-4-chlorobenzyl)pivalamide (Intermediate-103, 0.200 g, 0.419) in DMF was added at 0° C. and continued stirring at 5-10° C. for 2-3 h. The reaction mass was quenched in ice and pH adjusted to 6-7 and extracted with DCM. The organic layer was dried over anhydrous sodium sulphate and concentrated. The obtained crude product was purified by column chromatography on basic alumina, eluting with 5% MeOH:DCM to afford 0.020 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 1.23 (s, 9H), 1.79 (br s, 4H), 2.53 (br s, 4H), 3.66 (s, 2H), 4.48 (d, J=5.7 Hz, 2H), 6.08 (m, 1H), 7.26-7.54 (m, 5H), 7.79 (d, J=7.8 Hz, 2H); MS (m/z): 468.51 (M+H)+.

後処理

  1. stirringcontinued stirring at 5-10° C. for 2-3 h
  2. customThe reaction mass was quenched in ice
  3. extractionextracted with DCM
  4. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  5. concentrationconcentrated
  6. customThe obtained crude product
  7. customwas purified by column chromatography on basic alumina
  8. washeluting with 5% MeOH

出典と根拠

ORDレコード
ord-0b6fe7f845ee482caf8756c74cbd53f5
出典データセット
uspto-grants-2015_08
特許番号
US09096545B2

反応ノート

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