Potassium tert-butoxide → 1-[5-[2-(Ethylcarbamoylamino)-7-(pyrimidine-2-carbonylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylic acid

HRID 712305Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 712305
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([NH:16][C:17]([C:19]3[N:24]=[CH:23][CH:22]=[CH:21][N:20]=3)=[O:18])=[CH:14][C:13]([C:25]3[CH:26]=[N:27][C:28]([N:31]4[CH2:36][CH2:35][C:34]([CH3:42])([C:37]([O:39]CC)=[O:38])[CH2:33][CH2:32]4)=[N:29][CH:30]=3)=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2].CC(C)([O-])C.[K+]>CS(C)=O>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([NH:16][C:17]([C:19]3[N:20]=[CH:21][CH:22]=[CH:23][N:24]=3)=[O:18])=[CH:14][C:13]([C:25]3[CH:26]=[N:27][C:28]([N:31]4[CH2:32][CH2:33][C:34]([CH3:42])([C:37]([OH:39])=[O:38])[CH2:35][CH2:36]4)=[N:29][CH:30]=3)=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2]

Komponenten

4

Edukt 2

HCID 23665647Potassium tert-butoxideHCID 86664018Ethyl 1-[5-[2-(ethylcarbamoylamino)-7-(pyrimidine-2-carbonylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate

Produkt 1

HCID 569534031-[5-[2-(Ethylcarbamoylamino)-7-(pyrimidine-2-carbonylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylic acidAusbeute 5,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

Ethyl 1-[5-[2-(ethylcarbamoylamino)-7-(pyrimidine-2-carbonylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate (100 mg, 0.17 mmol) was dissolved in DMSO (0.5 mL) with stirring and potassium-t-butoxide (40 mg, 0.35 mmol) added. The reaction was allowed to stir at rt for 2 h. The reaction mixture was filtered and purified by preparative HPLC to afford Compound 146 as a solid (5 mg). 1H NMR (DMSO-d6): δ 11.01 (1H, s), 9.12 (2H, d, J=4.86 Hz), 8.77 (2H, s), 7.83 (1H, d, J=4.75 Hz), 7.82 (1H, t, J=1.44 Hz), 7.67 (1H, d, J=1.66 Hz), 7.01 (1H, s), 4.32 (2H, d, J=13.32 Hz), 3.22 (2H, p, J=7.59 Hz), 2.05 (2H, dd, J=13.04, 4.48 Hz), 1.42 (2H, t, J=11.27 Hz), 1.22 (3H, s), 1.13 (3H, dd, J=7.16, 7.16 Hz). MS: 562 [M+H]+.

Aufarbeitung

  1. stirringto stir at rt for 2 h
  2. filtrationThe reaction mixture was filtered
  3. custompurified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-253a3c3284cd469f8e4467e375db1016
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181234B2

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