1,2-Dichloroethane → Tert-butyl 1-(3-(3-amino-6-bromopyrazine-2-carboxamido)pyridin-4-yl)piperidin-3-ylcarbamate

HRID 69880

Reaktionsgleichung

Reaktionsgleichung von HRID 69880
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:9]1.[NH2:22][C:23]1[C:24]([C:30](O)=[O:31])=[N:25][C:26]([Br:29])=[CH:27][N:28]=1.C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.CCOC(C)=O>[NH2:22][C:23]1[C:24]([C:30]([NH:1][C:2]2[CH:3]=[N:4][CH:5]=[CH:6][C:7]=2[N:8]2[CH2:13][CH2:12][CH2:11][CH:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:20])[CH3:19])[CH2:9]2)=[O:31])=[N:25][C:26]([Br:29])=[CH:27][N:28]=1

Komponenten

7

Edukt 4

HCID 111,2-DichloroethaneHCID 181649HOAtHCID 185216003-Amino-6-bromopyrazine-2-carboxylic acidHCID 67130164Tert-butyl 1-(3-aminopyridin-4-yl)piperidin-3-ylcarbamate

Produkt 1

HCID 86669179Tert-butyl 1-(3-(3-amino-6-bromopyrazine-2-carboxamido)pyridin-4-yl)piperidin-3-ylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution containing 1 eq each of tert-butyl 1-(3-aminopyridin-4-yl)piperidin-3-ylcarbamate, 3-amino-6-bromopyrazine-2-carboxylic acid, HOAT and EDC in DMF, at a concentration of 0.5 M, was stirred for 60 hours. The solution was diluted with EtOAc and was washed with H2O (4×), NaCl(sat.), was dried over MgSO4, was filtered and the volatiles were removed in vacuo. After purification by silica gel chromatography (EtOAc eluant), tert-butyl 1-(3-(3-amino-6-bromopyrazine-2-carboxamido)pyridin-4-yl)piperidin-3-ylcarbamate was obtained (78%). LCMS (m/z): 492.2 (MH+); LC Rt=2.68 min.

Aufarbeitung

  1. washwas washed with H2O (4×), NaCl(sat.)
  2. dry with materialwas dried over MgSO4
  3. filtrationwas filtered
  4. customthe volatiles were removed in vacuo
  5. customAfter purification by silica gel chromatography (EtOAc eluant)

Quellen und Nachweise

ORD-Eintrag
ord-9592b42608d044f0b3167cbee937b637
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822497B2

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