Sodium Hydroxide → Regadenoson Impurity 1

HRID 1045316

Reaktionsgleichung

Reaktionsgleichung von HRID 1045316
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[N:19]=[C:18]3[C:14]([N:15]=[CH:16][N:17]3[C@H:20]3[C@H:24]([OH:25])[C@H:23]([OH:26])[C@@H:22]([CH2:27][OH:28])[O:21]3)=[C:13]([NH2:29])[N:12]=2)[CH:10]=1)=[O:5])C.[OH-].[Na+]>>[OH:25][C@@H:24]1[C@H:23]([OH:26])[C@@H:22]([CH2:27][OH:28])[O:21][C@H:20]1[N:17]1[CH:16]=[N:15][C:14]2[C:18]1=[N:19][C:11]([N:9]1[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]1)=[N:12][C:13]=2[NH2:29]

Komponenten

3

Edukt 2

HCID 14798Sodium HydroxideHCID 9865974Ethyl 1-(6-amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-2-yl)-1H-pyrazole-4-carboxylate

Produkt 1

HCID 9864495Regadenoson Impurity 1

Versuchsvorschrift

Compound 12 (0.05 mg, 0.12 mmol) was dissolved one equivalent of 1N NaOH. The solution was allowed to stir at Rt for 2 h, then acidified to pH 4. The resulting precipitate was filtered and washed with water and ether. 1HNMR (CD3OD) Δ 3.75 (m, 1H), 3.90 (m, 1H), 4.13 (d, 1H), 4.43 (d, 1H), 4.64 (m, 1H), 6.05 (d, 1H), 8.10 (s, 1H), 8.35 (s, 1H), 9.05 (s, 1H).

Aufarbeitung

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with water and ether

Quellen und Nachweise

ORD-Eintrag
ord-f0feb2cdbaea4ed6a34a7e60d160abae
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569260B2

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