Ethanolamine → HCID 66686018, Verbindung

HRID 1697385

Reaktionsgleichung

Reaktionsgleichung von HRID 1697385
[CH2:1]([CH2:3][NH2:4])[OH:2].[CH:5]1([NH:8][C:9](=[O:39])[C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([N:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24]4([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=5[O:33][CH2:34][C@H:35]5[CH2:37][O:36]5)[CH2:26][CH2:25]4)[C:18]3=[O:38])[CH:11]=2)[CH2:7][CH2:6]1>CN(C=O)C>[CH:5]1([NH:8][C:9](=[O:39])[C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([N:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24]4([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=5[O:33][CH2:34][C@H:35]([OH:36])[CH2:37][NH:4][CH2:3][CH2:1][OH:2])[CH2:25][CH2:26]4)[C:18]3=[O:38])[CH:11]=2)[CH2:6][CH2:7]1

Komponenten

4

Edukt 2

HCID 700EthanolamineHCID 86663253(R)-N-cyclopropyl-4-methyl-3-(3-(1-(2-(oxiran-2-ylmethoxy)phenyl)cyclopropylamino)-2-oxopyrazin-1(2H)-yl)benzamide

Produkt 1

HCID 66686018HCID 66686018, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Ethanolamine (1 mL) was added to N-cyclopropyl-4-methyl-3-{3-[(1-{2-[(2R)-oxiran-2-ylmethoxy]phenyl}cyclopropyl)amino]-2-oxopyrazin-1(2H)-yl}benzamide (Example 299a, 7.81 g) in DMF (3 mL). The reaction was heated at 50° C. overnight. The reaction mixture was partitioned between water and DCM. The combined organics were dried (MgSO4), filtered and evaporated. Purification by preparative HPLC (Xbridge column, eluting with a gradient of acetonitrile in 0.2% (v/v) aqueous ammonia) gave the title product (0.102 g) after solvent removal and trituration with diethyl ether.

Aufarbeitung

  1. customThe reaction mixture was partitioned between water and DCM
  2. dry with materialThe combined organics were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customPurification by preparative HPLC (Xbridge column
  6. washeluting with a gradient of acetonitrile in 0.2% (v/v) aqueous ammonia)

Quellen und Nachweise

ORD-Eintrag
ord-9dec82a4ed2545a5b8ea095ad73c4cd5
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163905B2

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