Water → Methyl (6-{4-[({5-[(2-fluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]piperidin-1-yl}pyridin-3-yl)acetate

HRID 1713879Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1713879
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:13][C:12]([C:14]([NH:16][CH:17]2[CH2:22][CH2:21][N:20]([C:23]3[N+:28]([O-])=[CH:27][C:26]([CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:25][CH:24]=3)[CH2:19][CH2:18]2)=[O:15])=[N:11][N:10]=1.O.[Cl-].[NH4+]>C1COCC1.CS(C)=O.[Zn]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:13][C:12]([C:14]([NH:16][CH:17]2[CH2:18][CH2:19][N:20]([C:23]3[N:28]=[CH:27][C:26]([CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:25][CH:24]=3)[CH2:21][CH2:22]2)=[O:15])=[N:11][N:10]=1

Komponenten

7

Edukt 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 59619585Methyl (6-{4-[({5-[(2-fluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]piperidin-1-yl}-1-oxidopyridin-3-yl)acetate

Produkt 1

HCID 59464268Methyl (6-{4-[({5-[(2-fluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]piperidin-1-yl}pyridin-3-yl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 679Dimethyl SulfoxideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methyl (6-{4-[({5-[(2-fluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]piperidin-1-yl}-1-oxidopyridin-3-yl)acetate (40 mg, 0.09 mmol) was stirred in THF (1.3 mL) at room temperature and water (1.3 mL) was added. Ammonium chloride (334 mg, 6.24 mmol) was added to the mixture followed by Zn dust (26 mg, 0.38 mmol). The reaction mixture was stirred overnight before diluting with 2 mL DMSO and filtering. The filtrate was purified by preparative HPLC to yield the title compound (Intermediate 102) as a gum; MS m/e MH+ 455.

Aufarbeitung

  1. filtrationfiltering
  2. customThe filtrate was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-59fcc9332a144c299ed189c0460f2ec8
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795283B2

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