Aspirin → 2-hydroxy-N-(2-(4-(isopropylsulfonyl)phenyl)-5-trityl-5H-pyrrolo[2,3-b]pyrazin-7-yl)benzamide

HRID 68666

Reaktionsgleichung

Reaktionsgleichung von HRID 68666
C([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=O)(=O)C.[CH:14]([S:17]([C:20]1[CH:25]=[CH:24][C:23]([C:26]2[N:27]=[C:28]3[C:34]([NH2:35])=[CH:33][N:32]([C:36]([C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C:29]3=[N:30][CH:31]=2)=[CH:22][CH:21]=1)(=[O:19])=[O:18])([CH3:16])[CH3:15].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN1CCOCC1>C(Cl)Cl>[OH:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([NH:35][C:34]1[C:28]2[C:29](=[N:30][CH:31]=[C:26]([C:23]3[CH:24]=[CH:25][C:20]([S:17]([CH:14]([CH3:16])[CH3:15])(=[O:19])=[O:18])=[CH:21][CH:22]=3)[N:27]=2)[N:32]([C:36]([C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:33]=1)=[O:9]

Komponenten

6

Edukt 4

HCID 2244AspirinHCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 711435912-(4-Isopropylsulfonylphenyl)-5-trityl-pyrrolo[2,3-b]pyrazin-7-amine

Produkt 1

HCID 711549822-hydroxy-N-(2-(4-(isopropylsulfonyl)phenyl)-5-trityl-5H-pyrrolo[2,3-b]pyrazin-7-yl)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A 5 mL microwave vial was charged with 2-acetoxybenzoic acid (33.87 mg, 0.1880 mmol) To this was added a solution of 2-(4-isopropylsulfonylphenyl)-5-trityl-pyrrolo[2,3-b]pyrazin-7-amine (100 mg, 0.1790 mmol), TBTU in DCM (1 mL) followed by PS-NMM. The reaction was shaken for 3 hours at ambient temperature then filtered and the resin washed with DCM (1 mL). This crude mixture was taken onto the next step as is.

Aufarbeitung

  1. filtrationthen filtered
  2. washthe resin washed with DCM (1 mL)

Quellen und Nachweise

ORD-Eintrag
ord-b41611152f6444abbee94ae2e2d8366d
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822469B2

Verknüpfte Notizen

Wird geladen…