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Sodium hydride → N-[6-Chloro-2-[(3-chloro-2-fluorobenzyl)thio]-4-pyrimidinyl]-4-methyl-1-piperazinesulfonamide

HRID 729666
ノート
印刷プレビュー

反応式

HRID 729666 の反応式
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([S:8]([NH2:11])(=[O:10])=[O:9])[CH2:4][CH2:3]1.[H-].[Na+].[Cl:14][C:15]1[CH:20]=[C:19](Cl)[N:18]=[C:17]([S:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[C:25]=2[F:31])[N:16]=1>CN(C=O)C>[Cl:14][C:15]1[N:16]=[C:17]([S:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[C:25]=2[F:31])[N:18]=[C:19]([NH:11][S:8]([N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)(=[O:10])=[O:9])[CH:20]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 143260054-Methylpiperazine-1-sulfonamideHCID 859280174,6-Dichloro-2-[(3-chloro-2-fluorobenzyl)thio]pyrimidine

生成物 1

HCID 86602819N-[6-Chloro-2-[(3-chloro-2-fluorobenzyl)thio]-4-pyrimidinyl]-4-methyl-1-piperazinesulfonamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a solution of the subtitle product of step i) (2.0 g) in dry DMF (20 ml) at 0° C. was added 60% sodium hydride (0.9 g) portionwise over 5 min. After further stirring at 0° C. for 30 min the subtitle product from step iii) (3.6 g) in DMF (10 ml) was added and the whole allowed to stir at room temperature for 24 h. The reaction mixture was carefully quenched with aqueous 2M hydrochloric acid until pH 7.4. The solvent was evaporated to dryness and the residue dissolved in a mixture of methanol/EtOAc and applied to an SCX column followed by further elution with EtOAc. This was then followed by elution with EtOAc/triethylamine mixtures and these fractions evaporated to dryness. The subtitle compound was obtained pure by trituration with Et2O and filtration, leaving a white solid. Yield: 1.5 g.

後処理

  1. additionwas added
  2. customThe reaction mixture was carefully quenched with aqueous 2M hydrochloric acid until pH 7.4
  3. customThe solvent was evaporated to dryness
  4. dissolutionthe residue dissolved in a mixture of methanol/EtOAc
  5. washfollowed by further elution with EtOAc
  6. washThis was then followed by elution with EtOAc/triethylamine mixtures
  7. customthese fractions evaporated to dryness

出典と根拠

ORDレコード
ord-b3d769ac89024d43b19891d2e3ce0af0
出典データセット
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07582644B2

反応ノート

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