Isonicotinoyl chloride hydrochloride → Hydrochloric Acid

HRID 1882594

Reaktionsgleichung

Reaktionsgleichung von HRID 1882594
[NH2:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[N:15]=[C:14]3[C:10]([N:11]=[CH:12][N:13]3[C@@H:16]3[CH2:20][C@H:19]([NH:21][C:22](=[O:25])[CH2:23][CH3:24])[C@@H:18]([OH:26])[C@H:17]3[OH:27])=[C:9]([NH:28][CH2:29][CH:30]([C:38]3[CH:43]=[CH:42][C:41]([OH:44])=[CH:40][CH:39]=3)[C:31]3[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=3)[N:8]=2)[CH2:3]1.[ClH:45].[C:46]([Cl:54])(=[O:53])[C:47]1[CH:52]=[CH:51][N:50]=[CH:49][CH:48]=1>C1COCC1.CN1C(=O)CCC1>[ClH:54].[ClH:45].[OH:44][C:41]1[CH:42]=[CH:43][C:38]([CH:30]([C:31]2[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=2)[CH2:29][NH:28][C:9]2[N:8]=[C:7]([N:4]3[CH2:5][CH2:6][C@@H:2]([NH:1][C:46](=[O:53])[C:47]4[CH:52]=[CH:51][N:50]=[CH:49][CH:48]=4)[CH2:3]3)[N:15]=[C:14]3[C:10]=2[N:11]=[CH:12][N:13]3[C@@H:16]2[CH2:20][C@H:19]([NH:21][C:22](=[O:25])[CH2:23][CH3:24])[C@@H:18]([OH:26])[C@H:17]2[OH:27])=[CH:39][CH:40]=1

Komponenten

6

Edukt 2

HCID 12262826Isonicotinoyl chloride hydrochlorideHCID 66630815N-((1S,2R,3S,4R)-4-{2-((R)-3-Amino-pyrrolidin-1-yl)-6-[2,2-bis-(4-hydroxy-phenyl)-ethylamino]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide

Produkt 2

HCID 313Hydrochloric AcidHCID 66629861HCID 66629861, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

A mixture comprising N-((1S,2R,3S,4R)-4-{2-((R)-3-amino-pyrrolidin-1-yl)-6-[2,2-bis-(4-hydroxy-phenyl)-ethylamino]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide (Example 22 step 4) (20 mg, 33 μmol) in THF (0.5 ml) and NMP (0.5 ml) is treated with TEA (13 mg, 0.13 mmol) followed by isonicotinoyl chloride hydrochloride (16 mg, 83 μmol). After stirring at room temperature for 2 hours, the solvent is removed in vacuo and purification by C-18 reverse phase column chromatography eluting with acetonitrile:water:HCl (0.1%) (gradient of 0 to 100% acetonitrile) yields the title compound. (MH+ 708.4)

Aufarbeitung

  1. customthe solvent is removed in vacuo and purification by C-18 reverse phase column chromatography
  2. washeluting with acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-1a44f918f635453098f935faaafa6e0a
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318750B2

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