Diethyl Ether → Zeneca ZM 224832

HRID 1111328Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1111328
[NH2:1][C:2]1[C:3]([C:10]([NH:12][CH2:13][CH2:14][N:15]([CH2:17][CH2:18][NH2:19])[CH3:16])=[O:11])=[N:4][C:5]([Cl:9])=[C:6]([NH2:8])[N:7]=1.[Br:20][C:21]1[C:22]([OH:34])=[C:23]([CH:32]=O)[C:24]2[CH2:25][CH2:26][C:27]([CH3:31])([CH3:30])[C:28]=2[CH:29]=1.[BH4-].[Na+].CCOCC>C(O)C.C(Cl)Cl>[NH2:1][C:2]1[C:3]([C:10]([NH:12][CH2:13][CH2:14][N:15]([CH2:17][CH2:18][NH:19][CH2:32][C:23]2[C:22]([OH:34])=[C:21]([Br:20])[CH:29]=[C:28]3[C:24]=2[CH2:25][CH2:26][C:27]3([CH3:31])[CH3:30])[CH3:16])=[O:11])=[N:4][C:5]([Cl:9])=[C:6]([NH2:8])[N:7]=1

Komponenten

7

Edukt 4

HCID 3283Diethyl EtherHCID 4311764Sodium borohydrideHCID 22152287HCID 22152287, VerbindungHCID 221522956-Bromo-1,1-dimethyl-5-hydroxyindan-4-carboxaldehyde

Produkt 1

HCID 195507Zeneca ZM 224832Ausbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 1.82 g (6.32 mmol) of 3,5-diamino-N-[2-[(2-aminoethyl)methylamino]ethyl]-6 -chloropyrazinecarboxamide (A) and 1.70 g (6.32 mmol) of 6-bromo-1,1-dimethyl-5-hydroxyindan-4-carboxaldehyde (B) in 70 ml of ethanol and 10 ml of methylene chloride was stirred at ambient temperature for 1 h. Sodium borohydride (0.29 g, 7.58 mmol) was added and the reaction mixture stirred for 15 min. The solution was evaporated and the residue was partitioned between water and methylene chloride The organic phase was dried and evaporated. The residue was chromatographed on silica gel (150 g) using 0.2:3:96.8 (v/v/v) ammonium hydroxide:methanol:methylene chloride as eluent. There was obtained 2.62 g (4.84 mmol, 77%) of the title compound after trituration with ether: mp 134°-136° C.

Aufarbeitung

  1. stirringthe reaction mixture stirred for 15 min
  2. customThe solution was evaporated
  3. customthe residue was partitioned between water and methylene chloride The organic phase
  4. customwas dried
  5. customevaporated
  6. customThe residue was chromatographed on silica gel (150 g)

Quellen und Nachweise

ORD-Eintrag
ord-e2df3113f06e40f8943cad1f83c218d0
Quelldatensatz
uspto-grants-1990_12
Patentnummer
US04980352

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