Acetic Acid → 6-(4-Chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-3-dimethylamino-8-isopropylhexahydropyrazino[1,2-a]pyrimidine-4,7-dione

HRID 1994397ノート

反応式

HRID 1994397 の反応式
Br.[Cl:2][C:3]1[CH:36]=[CH:35][C:6]([CH2:7][CH:8]2[N:13]3C(=O)C(N)[CH2:16][N:17]([S:18]([C:21]4[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=4[Cl:28])(=[O:20])=[O:19])[CH:12]3[CH2:11][N:10]([CH:31]([CH3:33])[CH3:32])[C:9]2=[O:34])=[CH:5][CH:4]=1.[C:37]([OH:40])(=O)[CH3:38].[CH2:41]=O.[C:43]([BH3-])#[N:44].[Na+]>CO.C1COCC1>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][CH:8]2[N:13]3[C:37](=[O:40])[CH:38]([N:44]([CH3:43])[CH3:41])[CH2:16][N:17]([S:18]([C:21]4[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=4[Cl:28])(=[O:20])=[O:19])[CH:12]3[CH2:11][N:10]([CH:31]([CH3:32])[CH3:33])[C:9]2=[O:34])=[CH:35][CH:36]=1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 686934646-(4-Chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-3-amino-8-isopropylhexahydropyrazino[1,2-a]pyrimidine-4,7-dione hydrobromide

生成物 1

HCID 591342116-(4-Chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-3-dimethylamino-8-isopropylhexahydropyrazino[1,2-a]pyrimidine-4,7-dione

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

200 mg of 6-(4-chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-3-amino-8-isopropylhexahydropyrazino[1,2-a]pyrimidine-4,7-dione hydrobromide (Example 2) were dissolved in 15 ml of methanol, and 600 μl of acetic acid were added. 0.5 ml of 37% strength aqueous formaldehyde and 3 ml of 1M sodium cyanoborohydride solution in THF were added to this solution. After 2 hours, the reaction mixture was evaporated, suspended in 5% Et3N in ethyl acetate and filtered through a small silica gel column. The eluent was evaporated, and the crude substance was dissolved in a mixture of acetonitrile and water and freeze dried. The pure title compound was removed after purification by HPLC. The system and process described under “general processes” was used for this. MW=586.10 (calculated, monoisotopic); measured value (M+H)+: 587.3.

後処理

  1. customthe reaction mixture was evaporated
  2. filtrationfiltered through a small silica gel column
  3. customThe eluent was evaporated
  4. dissolutionthe crude substance was dissolved in a mixture of acetonitrile and water and freeze
  5. customdried
  6. customThe pure title compound was removed
  7. customafter purification by HPLC

出典と根拠

ORDレコード
ord-dd8ab89909724d3a9861e42470417e72
出典データセット
uspto-grants-2010_01
特許番号
US07652007B2

反応ノート

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