L-Leucinol → 6-(2-Methoxy-ethoxy)-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acid ((S)-1-hydroxymethyl-3-methyl-butyl)-amide

HRID 639322

Reaction equation

HRID 639322 reaction equation
[OH:1][CH2:2][C@@H:3]([NH:8][C:9]([C:11]1[CH:16]=[N:15][C:14]([N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[C:13]([O:22][CH2:23][CH2:24]C)[N:12]=1)=[O:10])[CH2:4][CH:5]([CH3:7])[CH3:6].[CH3:26][O:27]CCOC1N=C(C(O)=O)C=NC=1N1CCCC1.N[C@@H](CC(C)C)CO>>[OH:1][CH2:2][C@@H:3]([NH:8][C:9]([C:11]1[CH:16]=[N:15][C:14]([N:17]2[CH2:18][CH2:19][CH2:20][CH2:21]2)=[C:13]([O:22][CH2:23][CH2:24][O:27][CH3:26])[N:12]=1)=[O:10])[CH2:4][CH:5]([CH3:7])[CH3:6]

Participants

4

Reactant 3

HCID 111307L-LeucinolHCID 248312586-Propoxy-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acid ((S)-1-hydroxymethyl-3-methyl-butyl)-amideHCID 685652096-(2-Methoxy-ethoxy)-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acid

Product 1

HCID 248314166-(2-Methoxy-ethoxy)-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acid ((S)-1-hydroxymethyl-3-methyl-butyl)-amide

Procedure

In analogy to the procedure described for the synthesis of 6-propoxy-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acid ((S)-1-hydroxymethyl-3-methyl-butyl)-amide (example 10, step d) the title compounds was prepared from 6-(2-methoxy-ethoxy)-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acid and (S)-2-amino-4-methyl-pentan-1-ol (commercially available). m/z (ES+): 367.3 (M+H).

Sources & evidence

ORD record
ord-f141c88bd95d47b9a013a51da8171121
Source dataset
uspto-grants-2010_04
Patent number
US07691863B2

Linked notes

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