1,2-Dichloroethane → Hydrochloric Acid

HRID 1882578Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1882578
[NH2:1][C@H:2]1[CH2:6][C@@H:5]([N:7]2[CH:15]=[N:14][C:13]3[C:8]2=[N:9][C:10]([N:31]2[CH2:35][CH2:34][C@@H:33]([NH:36][C:37]([NH:39][C:40]4[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=4)=[O:38])[CH2:32]2)=[N:11][C:12]=3[NH:16][CH2:17][CH:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:4]([OH:46])[C@@H:3]1[OH:47].[CH:48](=O)[CH2:49][CH3:50].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:66]CCCl>>[ClH:66].[ClH:66].[OH:46][C@@H:4]1[C@H:3]([OH:47])[C@@H:2]([NH:1][CH2:48][CH2:49][CH3:50])[CH2:6][C@H:5]1[N:7]1[CH:15]=[N:14][C:13]2[C:8]1=[N:9][C:10]([N:31]1[CH2:35][CH2:34][C@@H:33]([NH:36][C:37]([NH:39][C:40]3[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=3)=[O:38])[CH2:32]1)=[N:11][C:12]=2[NH:16][CH2:17][CH:18]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Komponenten

6

Edukt 4

HCID 111,2-DichloroethaneHCID 527PropanalHCID 5049666Sodium triacetoxyborohydrideHCID 666296911-{(R)-1-[9-((1R,2S,3R,4S)-4-amino-2,3-dihydroxy-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-pyrrolidin-3-yl}-3-pyridin-3-yl-urea

Produkt 2

HCID 313Hydrochloric AcidHCID 666303611-{(r)-1-[9-((1r,2s,3r,4s)-2,3-Dihydroxy-4-propylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9h-purin-2-yl]-pyrrolidin-3-yl}-3-pyridin-3-yl-urea hydrochloride

Versuchsvorschrift

A solution of 1-{(R)-1-[9-((1R,2S,3R,4S)-4-amino-2,3-dihydroxy-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-pyrrolidin-3-yl}-3-pyridin-3-yl-urea (Example 26 step 2) (17 mg, 26 mmol) in DCE (1 ml) is treated with propanaldehyde (1.5 mg, 26 mmol) and placed under an atmosphere of argon. Sodium triacetoxyborohydride (10 mg, 51 μmol) is added and the reaction mixture is stirred at room temperature overnight. The mixture is quenched with 2M NaOH (5 drops) and the solvent is removed in vacuo. The residue is purified by C-18 reverse phase column chromatography eluting with acetonitrile:water:HCl (0.1%) (gradient of 20 to 100% acetonitrile) to yield the title compound. (MH+ 677.14)

Aufarbeitung

  1. customThe mixture is quenched with 2M NaOH (5 drops)
  2. customthe solvent is removed in vacuo
  3. customThe residue is purified by C-18 reverse phase column chromatography
  4. washeluting with acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-9b2f206f69644ca18fced250087d2bd5
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318750B2

Notizen zur Reaktion

Wird geladen…