Triethylamine → 5-[4-[4-(6-chloro-2-pyrazinyl)-1-piperazinyl]butyl]tetrahydro-1H-thieno[3',4':3,4]cyclobuta[1,2-c]pyrrole-4,6(3H,5H)-dione 2,2 dioxide, hydrochloride

HRID 344788ノート

反応式

HRID 344788 の反応式
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[CH:9]2[CH:12]3[CH2:16][S:15](=[O:18])(=[O:17])[CH2:14][CH:13]3[CH:8]2[C:7]1=[O:19].Cl.[Cl:21][C:22]1[N:27]=[C:26]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH:25]=[N:24][CH:23]=1.C(N(CC)CC)C>CN(C)C=O>[ClH:21].[Cl:21][C:22]1[N:27]=[C:26]([N:28]2[CH2:29][CH2:30][N:31]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]3[C:10](=[O:11])[CH:9]4[CH:12]5[CH2:16][S:15](=[O:18])(=[O:17])[CH2:14][CH:13]5[CH:8]4[C:7]3=[O:19])[CH2:32][CH2:33]2)[CH:25]=[N:24][CH:23]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 198421MK-212 hydrochlorideHCID 679226745-(4-bromobutyl)tetrahydro-1H-thieno-[3',4':3,4]cyclobuta[1,2-c]pyrrole-4,6(3H,5H)dione 2,2-dioxide

生成物 1

HCID 140865415-[4-[4-(6-chloro-2-pyrazinyl)-1-piperazinyl]butyl]tetrahydro-1H-thieno[3',4':3,4]cyclobuta[1,2-c]pyrrole-4,6(3H,5H)-dione 2,2 dioxide, hydrochloride

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 2.0 g of 5-(4-bromobutyl)tetrahydro-1H-thieno-[3',4':3,4]cyclobuta[1,2-c]pyrrole-4,6(3H,5H)dione 2,2-dioxide in 50 ml of dimethylformamide is added to a stirred solution 2.0 g (0.007 mol) of 1-(6-chloro-2-pyrazinyl)-piperazine hydrochloride and 4 ml of triethylamine. The reaction mixture is stirred overnight and the solvent is removed under vacuum. The residue is partitioned between water and methlene chloride. The methylene chloride extracts are combined, washed with brine and dried over anhydrous sodium sulfate. Filtration and roto-evaporation gives the crude free base. Preparative HPLC [silica gel; ethyl acetate:methylene chloride (9:1)] followed by evaporation of the appropriate fractions (TLC Rf=0.4), treatment with ethanolic hydrogen chloride and recrystallization from ethanol gives the title compound: m.p. 154°-157° C.

後処理

  1. customthe solvent is removed under vacuum
  2. customThe residue is partitioned between water and methlene chloride
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationFiltration and roto-evaporation
  6. customgives the crude free base
  7. customPreparative HPLC [silica gel; ethyl acetate:methylene chloride (9:1)] followed by evaporation of the appropriate fractions (TLC Rf=0.4), treatment with ethanolic hydrogen chloride and recrystallization from ethanol

出典と根拠

ORDレコード
ord-22f4fe30766a4172b0be42fbef327d49
出典データセット
uspto-grants-1991_10
特許番号
US05053508

反応ノート

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