Isobutyraldehyde → Ethyl cis(+/-)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-[(2-methylpropyl)amino]piperidin-1-yl)-1,3-benzothiazole-7-carboxylate

HRID 43547

Reaktionsgleichung

Reaktionsgleichung von HRID 43547
[NH2:1][C@H:2]1[C@@H:7]([NH:8][C:9]([C:11]2[NH:12][C:13]([CH2:17][CH3:18])=[C:14]([Cl:16])[N:15]=2)=[O:10])[CH2:6][CH2:5][N:4]([C:19]2[S:20][C:21]3[C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:26][CH:25]=[CH:24][C:22]=3[N:23]=2)[CH2:3]1.[CH3:33][CH:34]([CH3:37])[CH:35]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[Cl:16][C:14]1[N:15]=[C:11]([C:9]([NH:8][C@H:7]2[CH2:6][CH2:5][N:4]([C:19]3[S:20][C:21]4[C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:26][CH:25]=[CH:24][C:22]=4[N:23]=3)[CH2:3][C@H:2]2[NH:1][CH2:33][CH:34]([CH3:37])[CH3:35])=[O:10])[NH:12][C:13]=1[CH2:17][CH3:18]

Komponenten

4

Edukt 3

HCID 6561IsobutyraldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86648558Ethyl cis(+/-)-2-(3-amino-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3-benzothiazole-7-carboxylate2×

Produkt 1

HCID 86648564Ethyl cis(+/-)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-[(2-methylpropyl)amino]piperidin-1-yl)-1,3-benzothiazole-7-carboxylateAusbeute 88 %

Versuchsvorschrift

The same operation as in Example (77d) was performed using ethyl cis(±)-2-(3-amino-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3-benzothiazole-7-carboxylate obtained by the method described in Example (81e) (30 mg, 0.063 mmol), 2-methylpropanal (7 μL, 0.077 mmol) and sodium (triacetoxy)borohydride (60 mg, 0.28 mmol), to obtain 29.6 mg of the title compound as a white solid (88%).

Aufarbeitung

  1. customobtained by the method

Quellen und Nachweise

ORD-Eintrag
ord-69b3acf1fff445be965604e0a901a0b2
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536197B2

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