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Diisopropylethylamine → Ethyl (2S)-2-(naphthalene-1-sulfonylamino)-3-{6-[4-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)piperidin-1-yl]purin-9-yl}propionate

HRID 1612377
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1612377
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:11][C@H:12]([NH:18][S:19]([C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1)(=[O:21])=[O:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14].[NH:32]1[CH2:37][CH2:36][CH:35]([C:38]2[N:47]=[C:46]3[C:41]([CH2:42][CH2:43][CH2:44][NH:45]3)=[CH:40][CH:39]=2)[CH2:34][CH2:33]1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[C:22]1([S:19]([NH:18][C@@H:12]([CH2:11][N:6]2[CH:5]=[N:4][C:3]3[C:7]2=[N:8][CH:9]=[N:10][C:2]=3[N:32]2[CH2:37][CH2:36][CH:35]([C:38]3[CH:39]=[CH:40][C:41]4[CH2:42][CH2:43][CH2:44][NH:45][C:46]=4[N:47]=3)[CH2:34][CH2:33]2)[C:13]([O:15][CH2:16][CH3:17])=[O:14])(=[O:21])=[O:20])[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1
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Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 113903267-(4-Piperidinyl)-1,2,3,4-tetrahydro[1,8]naphthyridineHCID 12046028ethyl (2S)-3-(6-chloropurin-9-yl)-2-(naphthalene-1-sulfonylamino)propionate

Produkt 1

HCID 12046030Ethyl (2S)-2-(naphthalene-1-sulfonylamino)-3-{6-[4-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)piperidin-1-yl]purin-9-yl}propionate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

3.21 g of ethyl (2S)-3-(6-chloropurin-9-yl)-2-(naphthalene-1-sulfonylamino)propionate (Example 2) in 20 ml of abs. DMF were treated with 4.0 g of 7-(piperidin-4-yl)-1,2,3,4-tetrahydro-[1,8]naphthyridine and 3.88 g of diisopropylethylamine, and the mixture was stirred at 70° C. for 3 h. The solvent was distilled off in vacuo, the residue was taken up in EA and the mixture was extracted three times with water. The aqueous phases were extracted three times with DCM. The combined organic phases were dried over MgSO4 and filtered, and the solvent was distilled off in vacuo. For purification, the residue was chromatographed over silica gel (DCM/CH3OH/CH3COOH/H2O 95:5:0.5:0.5). Yield: 3.29 g.

Aufarbeitung

  1. distillationThe solvent was distilled off in vacuo
  2. extractionthe mixture was extracted three times with water
  3. extractionThe aqueous phases were extracted three times with DCM
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. filtrationfiltered
  6. distillationthe solvent was distilled off in vacuo
  7. customFor purification
  8. customthe residue was chromatographed over silica gel (DCM/CH3OH/CH3COOH/H2O 95:5:0.5:0.5)

Quellen und Nachweise

ORD-Eintrag
ord-26b8035f5fe247f7bf3597145bec60dc
Quelldatensatz
uspto-grants-2006_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06992187B2

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