Triethylamine → (5)-Tert-butyl 3-(4-(5-bromo-1h-pyrrolo [2,3-b]pyridin-4-yl)piperazin-1-yl)-2-(4-chlorophenyl)-3-oxopropyl(isopropyl)carbamate

HRID 79520Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 79520
N[C@H](CC1C=CC(Cl)=CC=1)[C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[C:16]([Br:17])=[CH:15][N:14]=[C:13]3[NH:18][CH:19]=[CH:20][C:12]=23)[CH2:7][CH2:6]1)=[O:4].[C:29]([O:33][C:34]([N:36]([CH:49]([CH3:51])[CH3:50])[CH2:37][C@H:38]([C:42]1[CH:47]=[CH:46][C:45]([Cl:48])=[CH:44][CH:43]=1)C(O)=O)=[O:35])([CH3:32])([CH3:31])[CH3:30].C1C=CC2N(O)N=NC=2C=1.O.CCN=C=NCCCN(C)C.C(N(CC)CC)C>C(Cl)Cl>[Br:17][C:16]1[C:11]([N:8]2[CH2:7][CH2:6][N:5]([C:3](=[O:4])[C@@H:38]([C:42]3[CH:43]=[CH:44][C:45]([Cl:48])=[CH:46][CH:47]=3)[CH2:37][N:36]([CH:49]([CH3:51])[CH3:50])[C:34](=[O:35])[O:33][C:29]([CH3:31])([CH3:32])[CH3:30])[CH2:10][CH2:9]2)=[C:12]2[CH:20]=[CH:19][NH:18][C:13]2=[N:14][CH:15]=1

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 44123672(R)-2-amino-1-(4-(5-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-3-(4-chlorophenyl)propan-1-oneHCID 59564929(2S)-3-[tert-butoxycarbonyl(isopropyl)amino]-2-(4-chlorophenyl)propanoic acid

Produkt 1

HCID 68764847(5)-Tert-butyl 3-(4-(5-bromo-1h-pyrrolo [2,3-b]pyridin-4-yl)piperazin-1-yl)-2-(4-chlorophenyl)-3-oxopropyl(isopropyl)carbamateAusbeute 60,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

5-Bromo-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine dihydrochloride (0.100 g, 0.282 mmol, see Example 1), (S)-3-(tert-butoxycarbonyl(isopropyl)amino)-2-(4-chlorophenyl)propanoic acid (0.145 g, 0.424 mmol, see Example H), HOBT-H2O (0.0606 g, 0.395 mmol), EDCI (0.0704 g, 0.367 mmol), and triethylamine (0.0394 mL, 0.282 mmol) were stirred in DCM (5 mL) at room temperature for 5 hours. The reaction was then quenched with saturated Na2CO3 and extracted into DCM. The organics were dried, filtered, and concentrated to give the crude product. Purification (500:6 DCM:MeOH) gave (S)-tert-butyl 3-(4-(5-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-2-(4-chlorophenyl)-3-oxopropyl(isopropyl)carbamate (0.103 g, 60.2% yield).

Aufarbeitung

  1. customThe reaction was then quenched with saturated Na2CO3
  2. extractionextracted into DCM
  3. customThe organics were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give the crude product
  7. customPurification (500:6 DCM:MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-8a256ade946d4432a0c2d8bea1e9b971
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841304B2

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