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

HRID 1425021

Reaktionsgleichung

Reaktionsgleichung von HRID 1425021
[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.[C:33]1(=O)[CH2:37][CH2:36][CH2:35][CH2:34]1.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][CH:33]2[CH2:37][CH2:36][CH2:35][CH2:34]2)=[O:10])[NH:12][C:13]=1[CH2:17][CH3:18]

Komponenten

4

Edukt 3

HCID 8452CyclopentanoneHCID 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 86648565Ethyl cis(+/-)-2-[4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-(cyclopentylamino)piperidin-1-yl]-1,3-benzothiazole-7-carboxylateAusbeute 75 %

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), cyclopentanone (33.5 μL, 0.038 mmol) and sodium (triacetoxy)borohydride (175 mg, 0.83 mmol), to obtain 25.6 mg of the title compound as a white solid (75%).

Aufarbeitung

  1. customobtained by the method

Quellen und Nachweise

ORD-Eintrag
ord-8ad9246fdb9b4e9ab2e9a938f00c77c5
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927588B2

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