1-Heptanamine → HCID 54427198、化合物

HRID 1029734ノート

反応式

HRID 1029734 の反応式
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([OH:11])[CH:9]=2)[N:4]([N:12]([CH2:19][CH2:20][CH3:21])[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[CH:3]=1.[C:22]([N:29]1[CH:33]=[CH:32]N=C1)(N1C=CN=C1)=[O:23].[CH2:34](N)[CH2:35][CH2:36][CH2:37][CH2:38]CC.C(=O)(O)[O-].[Na+]>C1COCC1.C(O)(=O)C>[CH2:33]([NH:29][C:22](=[O:23])[O:11][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[N:4]([N:12]([CH2:19][CH2:20][CH3:21])[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)[CH:3]=[C:2]2[CH3:1])[CH2:32][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]

参加物

7

反応物 4

HCID 81271-Heptanamine2 回HCID 682631,1'-CarbonyldiimidazoleHCID 516892Sodium BicarbonateHCID 190723493-Methyl-1-[propyl(pyridin-4-yl)amino]-1H-indol-5-ol

生成物 1

HCID 54427198HCID 54427198、化合物

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒3 回HCID 8028Tetrahydrofuran溶媒3 回

実験手順

To a solution consisting of 3-methyl-1-(propyl-4-pyridinylamino)-1H-indol-5-ol (2.23 g) and tetrahydrofuran (53 ml) was added 1,1'-carbonyldiimidazole (2.57 g) at room temperature with stirring under nitrogen. Stirring was continued for 96 hours, at which time acetic acid (1.54 ml) was added. To the resulting reaction mixture was added a solution consisting of heptyl amine (1.76 ml), acetic acid (0.71 ml) and THF (5 ml). After stirring for 24 hours, an additional solution of heptyl amine (1.17 ml), acetic acid (0.48 ml) and THF (5 ml) was added and stirring continued for 3 hours. The reaction mixture was poured into a dilute aqueous sodium bicarbonate solution and the product extracted with ether (3x). The combined organic layer was washed with brine and dried (MgSO4). Filtration, concentration and purification via flash column chromatography (silica gel, 2% Et3N/ether) afforded 1.60 g of the desired carbamate after recrystallization from ether/pentane, m.p. 102°-104° C.

後処理

  1. stirringStirring
  2. additionwas added
  3. customTo the resulting reaction mixture
  4. additionwas added a solution
  5. stirringAfter stirring for 24 hours
  6. stirringstirring
  7. extractionthe product extracted with ether (3x)
  8. washThe combined organic layer was washed with brine
  9. dry with materialdried (MgSO4)
  10. filtrationFiltration, concentration and purification via flash column chromatography (silica gel, 2% Et3N/ether)

出典と根拠

ORDレコード
ord-632b7a7858044aaeae947375b529172b
出典データセット
uspto-grants-1992_04
特許番号
US05102891

反応ノート

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