Triethylamine → HCID 86649730, Verbindung

HRID 386758

Reaktionsgleichung

Reaktionsgleichung von HRID 386758
[Br:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]([C:14]([NH:16][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:15])=[C:10]([OH:25])[C:9]3[CH2:26][NH:27][CH:28]([CH3:29])[C:8]2=3)=[CH:4][CH:3]=1.Cl.C1(C2C=CC=CC=2)C=CC(CN2C(=O)C(C(NCC(OC(C)(C)C)=O)=O)=C(O)C3CNCC2=3)=CC=1.[S:68]1[CH:72]=[C:71]([C:73](Cl)=[O:74])[N:70]=[CH:69]1.CCN(CC)CC>CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]([C:14]([NH:16][CH2:17][C:18]([O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[O:19])=[O:15])=[C:10]([OH:25])[C:9]3[CH2:26][N:27]([C:73]([C:71]4[N:70]=[CH:69][S:68][CH:72]=4)=[O:74])[CH:28]([CH3:29])[C:8]2=3)=[CH:30][CH:31]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 155721001,3-Thiazole-4-carbonyl chlorideHCID 66850853HCID 66850853, VerbindungHCID 71251569HCID 71251569, Verbindung

Produkt 1

HCID 86649730HCID 86649730, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To tert-butyl N-{[1-(4-bromobenzyl)-4-hydroxy-7-methyl-2-oxo-2,5,6,7-tetrahydro-1H-pyrrolo[3,4-b]pyridin-3-yl]carbonyl}glycinate (1.344 g, 2.73 mmol, prepared in similar fashion to Intermediate 6 utilizing the appropriate starting materials) was added the product of Step A (0.403 g, 2.73 mmol) and NEt3 (0.38 mL, 2.73 mL). The reaction stirred at rt for about 17 h and was then diluted with EtOAc and washed with aq Na2CO3 (2 M) and brine. The concentrated residue was purified by flash chromatography on silica gel gradient eluted with 0-65% EtOAc/hexane to afford the product.

Aufarbeitung

  1. washwashed with aq Na2CO3 (2 M) and brine
  2. customThe concentrated residue was purified by flash chromatography on silica gel gradient
  3. washeluted with 0-65% EtOAc/hexane
  4. customto afford the product

Quellen und Nachweise

ORD-Eintrag
ord-cbf17ac683f7465ea5188d892c0f1c8b
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372863B2

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