1-Heptanamine → HCID 54427198, 화합물

HRID 1029734노트

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HRID 1029734 반응식
[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]

참가 물질

7

반응물 4

HCID 81271-Heptanamine2회HCID 682631,1'-CarbonyldiimidazoleHCID 516892Sodium BicarbonateHCID 190723493-Methyl-1-[propyl(pyridin-4-yl)amino]-1H-indol-5-ol

생성물 1

HCID 54427198HCID 54427198, 화합물

시약·촉매·용매 2

HCID 176Acetic Acid용매3회HCID 8028Tetrahydrofuran용매3회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-632b7a7858044aaeae947375b529172b
출처 데이터셋
uspto-grants-1992_04
특허 번호
US05102891

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