Hydrochloric Acid → 2-Chloro-5-[[2-(2-hydroxy-ethylamino)-ethylamino]-methyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide dihydrochloride

HRID 719624ノート

反応式

HRID 719624 の反応式
[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH:22]=O)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5].[NH2:24][CH2:25][CH2:26][NH:27][CH2:28][CH2:29][OH:30].[BH4-].[Na+].[ClH:33]>C(O)C.CO.O1CCOCC1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[ClH:1].[ClH:33].[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH2:22][NH:24][CH2:25][CH2:26][NH:27][CH2:28][CH2:29][OH:30])=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:15][CH:14]3[CH2:13][CH:12]([CH2:11][CH:10]([CH2:16]3)[CH2:9]1)[CH2:17]2)=[O:5]

参加物

10

反応物 4

HCID 313Hydrochloric AcidHCID 8112N-(2-Hydroxyethyl)ethylenediamineHCID 4311764Sodium borohydrideHCID 120853462-Chloro-5-formyl-N-(tricyclo [3.3.1.13,7]dec-1-ylmethyl)-benzamide

生成物 1

HCID 98918542-Chloro-5-[[2-(2-hydroxy-ethylamino)-ethylamino]-methyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide dihydrochloride

試薬・触媒・溶媒 5

HCID 6101p-Toluenesulfonic acid触媒HCID 702Ethanol溶媒HCID 887Methanol溶媒HCID 1140Toluene溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
0 °C

実験手順

A mixture of 2-chloro-5-formyl-N-(tricyclo [3.3.1.13,7]dec-1-ylmethyl)-benzamide (0.244 g, Example 1b), 2-(2-aminoethylamino)-ethanol (0.154 g), p-toluenesulfonic acid (0.005 g) and toluene (30 ml) were refluxed together under Dean-Stark conditions for 3 hs, cooled and concentrated under reduced pressure to give an oil. This was dissolved in ethanol (30 ml) and cooled to 0° C. under a nitrogen atmosphere. Solid sodium borohydride (0.030 g) was added portionwise to this and the mixture stirred at room temperature for 30 min. The mixture was concentrated under reduced pressure and the residue purified by column chromatography over silica gel (eluting with 7:3:0.3 dichloromethane/methanol/35% aqueous ammonia) to give the free base. This was dissolved in methanol (10 ml) and treated with 4M hydrochloric acid in dioxane (4 ml) to give a solid precipitate. This was filtered off and washed with diethyl ether to afford the title compound as a solid (0.165 g).

後処理

  1. temperaturewere refluxed together under Dean-Stark conditions for 3 hs
  2. temperaturecooled
  3. concentrationconcentrated under reduced pressure
  4. customto give an oil
  5. concentrationThe mixture was concentrated under reduced pressure
  6. customthe residue purified by column chromatography over silica gel (eluting with 7:3:0.3 dichloromethane/methanol/35% aqueous ammonia)
  7. customto give the free base
  8. customto give a solid precipitate
  9. filtrationThis was filtered off
  10. washwashed with diethyl ether

出典と根拠

ORDレコード
ord-29447754eec44891bf73f3f0ebfbb101
出典データセット
uspto-grants-2006_11
特許番号
US07132457B2

反応ノート

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