1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (S)-(1-(4-chlorobenzyl)-1H-indol-2-yl)(4-(2-(hydroxymethyl)pyrrolidine-1-carbonyl)piperidin-1-yl)methanone

HRID 83608

Reaktionsgleichung

Reaktionsgleichung von HRID 83608
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([N:18]2[CH2:23][CH2:22][CH:21]([C:24]([OH:26])=O)[CH2:20][CH2:19]2)=[O:17])=[CH:4][CH:3]=1.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[NH:59]1[CH2:65][CH2:64][CH2:63][C@H:60]1[CH2:61][OH:62]>C(Cl)Cl.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([N:18]2[CH2:19][CH2:20][CH:21]([C:24]([N:59]3[CH2:65][CH2:64][CH2:63][C@H:60]3[CH2:61][OH:62])=[O:26])[CH2:22][CH2:23]2)=[O:17])=[CH:27][CH:28]=1

Komponenten

9

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 640091L-ProlinolHCID 573857961-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid

Produkt 1

HCID 68379902(S)-(1-(4-chlorobenzyl)-1H-indol-2-yl)(4-(2-(hydroxymethyl)pyrrolidine-1-carbonyl)piperidin-1-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid (100 mg, 0.252 mmol), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (97 mg, 0.504 mmol), and 1-Hydroxybenzotriazole (68 mg, 0.504 mmol) were dissolved in 3.0 mL of DCM. The reaction was allowed to stir for 10 minutes before N,N-Diisopropylethylamine (88 μL, 0.504 mmol) and L-prolinol (49.5 μL, 0.504 mmol) were added. The reaction was allowed to stir overnight. The reaction was diluted with water and ethyl acetate. The layers were separated and the organic layer was washed with another aliquot of water. The ethyl acetate layer was washed with saturated citric acid, saturated sodium bicarbonate, and saturated sodium chloride. The organic layer was dried over magnesium sulfate, filtered and concentrated. The crude material was purified in silica gel using the gradient 100% DCM to 5% 7M NH3 in methanol diluted with 95% DCM. After purification, pure white solid was obtained. Yield: 118 mg (White solid)

Aufarbeitung

  1. additionwere added
  2. customThe layers were separated
  3. washthe organic layer was washed with another aliquot of water
  4. washThe ethyl acetate layer was washed with saturated citric acid, saturated sodium bicarbonate, and saturated sodium chloride
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was purified in silica gel using the gradient 100% DCM to 5% 7M NH3 in methanol
  9. additiondiluted with 95% DCM
  10. customAfter purification
  11. custompure white solid was obtained

Quellen und Nachweise

ORD-Eintrag
ord-fad07df9c30e4a0d977047edc950748a
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846684B2

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