HCID 87222433, Verbindung → HCID 87222515, Verbindung

HRID 712276Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 712276
C(O[K])(C)(C)C.[CH2:7]([NH:9][C:10]([NH:12][C:13]1[S:14][C:15]2[C:21](/[C:22](/[CH3:26])=[N:23]/[O:24][CH3:25])=[CH:20][C:19]([C:27]3[CH:28]=[N:29][C:30]([N:33]4[CH2:38][CH2:37][C:36]([CH3:44])([C:39]([O:41]CC)=[O:40])[CH2:35][CH2:34]4)=[N:31][CH:32]=3)=[CH:18][C:16]=2[N:17]=1)=[O:11])[CH3:8]>CS(C)=O>[CH2:7]([NH:9][C:10]([NH:12][C:13]1[S:14][C:15]2[C:21](/[C:22](/[CH3:26])=[N:23]/[O:24][CH3:25])=[CH:20][C:19]([C:27]3[CH:32]=[N:31][C:30]([N:33]4[CH2:38][CH2:37][C:36]([CH3:44])([C:39]([OH:41])=[O:40])[CH2:35][CH2:34]4)=[N:29][CH:28]=3)=[CH:18][C:16]=2[N:17]=1)=[O:11])[CH3:8]

Komponenten

4

Edukt 2

HCID 87222433HCID 87222433, VerbindungHCID 178418922HCID 178418922, Verbindung

Produkt 1

HCID 87222515HCID 87222515, VerbindungAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

tBuOK (124 mg, 1.11 mmol) was added to a solution of ethyl 1-[5-[2-(ethylcarbamoylamino)-7-[(E)-N-methoxy-C-methyl-carbonimidoyl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate in DMSO (4 mL). The mixture was stirred at ambient temperature for 2 h after which time LCMS indicated clean conversion to the acid. The mixture was filtered through cotton wool to remove solid particulates and purified by preparative HPLC to give Compound 88 as a white solid, 76 mg, 40% yield over 2 steps. 1H NMR (DMSO-d6): δ 10.89 (1H, s), 8.85 (2H, s), 7.95 (1H, d, J=1.62 Hz), 7.76 (1H, d, J=1.69 Hz), 7.16 (1H, t, J=5.50 Hz), 4.32 (2H, dt, J=13.67, 4.40 Hz), 4.09 (3H, s), 3.38 (2H, ddd, J=13.49, 10.48, 3.40 Hz), 3.23 (2H, p, J=6.71 Hz), 2.42 (3H, s), 2.05 (2H, dt, J=13.34, 3.66 Hz), 1.41 (2H, ddd, J=13.34, 10.04, 3.92 Hz), 1.21 (3H, s), 1.14 (3H, t, J=7.15 Hz). MS: 512 [M+H]+.

Aufarbeitung

  1. filtrationThe mixture was filtered through cotton wool
  2. customto remove solid particulates
  3. custompurified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-c049c60c51ae4d60aa26597ff75e326c
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181234B2

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