Diisopropylethylamine → 6-Propoxy-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acid ((S)-1-hydroxymethyl-3-methyl-butyl)-amide

HRID 639316

Reaktionsgleichung

Reaktionsgleichung von HRID 639316
[CH2:1]([O:4][C:5]1[N:10]=[C:9]([C:11]([OH:13])=O)[CH:8]=[N:7][C:6]=1[N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)[CH2:2][CH3:3].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:50][C@@H:51]([CH2:54][CH:55]([CH3:57])[CH3:56])[CH2:52][OH:53]>CN(C=O)C.C(O)=O>[OH:53][CH2:52][C@@H:51]([NH:50][C:11]([C:9]1[CH:8]=[N:7][C:6]([N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[C:5]([O:4][CH2:1][CH2:2][CH3:3])[N:10]=1)=[O:13])[CH2:54][CH:55]([CH3:57])[CH3:56]

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 111307L-LeucinolHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 685674456-Propoxy-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acid

Produkt 1

HCID 248312586-Propoxy-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acid ((S)-1-hydroxymethyl-3-methyl-butyl)-amideAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 284Formic AcidLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 6 mg (0.024 mmol) 6-propoxy-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acid, 9.3 mg (0.029 mmol) TBTU, 9.3 mg (0.072 mmol) DIPEA and 4.2 mg (0.036 mmol) (S)-2-amino-4-methyl-pentan-1-ol (commercially available) in 1 mL DMF was shaken at room temperature for 16 h. After addition of formic acid the mixture was subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and formic acid. The combined product fractions were evaporated to yield 2 mg (24%) of the title compound. m/z (ES+): 351.5 (M+H).

Aufarbeitung

  1. customwas subjected to purification by preparative HPLC on reversed phase
  2. washeluting with a gradient
  3. customformed from acetonitrile, water and formic acid
  4. customThe combined product fractions were evaporated

Quellen und Nachweise

ORD-Eintrag
ord-13572c0ed70f480daa3350330e68eace
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691863B2

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