Potassium tert-butoxide → 1-(5-(2-(3-Ethylureido)-7-(picolinamido)benzo[d]thiazol-5-yl)pyrimidin-2-yl)-4-methylpiperidine-4-carboxylic acid

HRID 712310

Reaktionsgleichung

Reaktionsgleichung von HRID 712310
[CH2:1]([NH:3][C:4](=[O:42])[NH:5][C:6]1[S:7][C:8]2[C:14]([NH:15][C:16](=[O:23])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)=[CH:13][C:12]([C:24]3[CH:25]=[N:26][C:27]([N:30]4[CH2:35][CH2:34][C:33]([CH3:41])([C:36]([O:38]CC)=[O:37])[CH2:32][CH2:31]4)=[N:28][CH:29]=3)=[CH:11][C:9]=2[N:10]=1)[CH3:2].CC(C)([O-])C.[K+]>CS(C)=O>[CH2:1]([NH:3][C:4](=[O:42])[NH:5][C:6]1[S:7][C:8]2[C:14]([NH:15][C:16](=[O:23])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)=[CH:13][C:12]([C:24]3[CH:25]=[N:26][C:27]([N:30]4[CH2:35][CH2:34][C:33]([CH3:41])([C:36]([OH:38])=[O:37])[CH2:32][CH2:31]4)=[N:28][CH:29]=3)=[CH:11][C:9]=2[N:10]=1)[CH3:2]

Komponenten

4

Edukt 2

HCID 23665647Potassium tert-butoxideHCID 86664022Ethyl 1-(5-(2-(3-ethylureido)-7-(picolinamido)benzo[d]thiazol-5-yl)pyrimidin-2-yl)-4-methylpiperidine-4-carboxylate

Produkt 1

HCID 866640231-(5-(2-(3-Ethylureido)-7-(picolinamido)benzo[d]thiazol-5-yl)pyrimidin-2-yl)-4-methylpiperidine-4-carboxylic acidAusbeute 30,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

Ethyl 1-(5-(2-(3-ethylureido)-7-(picolinamido)benzo[d]thiazol-5-yl)pyrimidin-2-yl)-4-methylpiperidine-4-carboxylate (100 mg, 0.17 mmol) was dissolved in DMSO (2 ml) with stirring and potassium-t-butoxide (76 mg, 0.68 mmol) added. The reaction was stirred at rt for 2 h. The reaction mixture was filtered and purified by preparative HPLC to afford Compound 149 as a solid (29 mg, 98% purity by LC-MS) (30%). 1H NMR (DMSO-d6): δ 10.87 (1H, s), 8.84 (1H, d, J=4.78 Hz), 8.78 (2H, s), 8.25 (1H, d, J=7.82 Hz), 8.15 (1H, td, J=7.67, 1.67 Hz), 7.81 (1H, s), 7.77 (1H, dd, J=7.65, 4.87 Hz), 7.73 (1H, s), 6.86 (1H, s), 4.32 (2H, dt, J=13.67, 4.43 Hz), 3.22 (2H, p, J=6.69 Hz), 2.05 (2H, dt, J=13.55, 3.74 Hz), 1.43 (2H, ddd, J=13.38, 9.93, 3.91 Hz), 1.22 (3H, s), 1.13 (3H, t, J=7.15 Hz). MS: 561 [M+H]+.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-5f97fd8972344fa5a03e055ba3937859
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181234B2

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