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Dimethylformamide → N-(2-Amino-1-cyano-2-oxoethyl)-5-chloro-6-[4-(2-oxo-2H-3,1-benzoxazin-1(4H)-yl)piperidin-1-yl]pyridine-3-carboxamide

HRID 2414339
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2414339
[Cl:1][C:2]1[CH:3]=[C:4]([C:25](O)=[O:26])[CH:5]=[N:6][C:7]=1[N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[CH2:17][O:16][C:15]2=[O:24])[CH2:10][CH2:9]1.C(Cl)(=O)C(Cl)=O.C[N:35](C)[CH:36]=[O:37].C([N:42](CC)[CH:43]([CH3:45])C)(C)C.C[N:49]1CCCC1=O>ClCCl>[NH2:35][C:36](=[O:37])[CH:45]([NH:49][C:25]([C:4]1[CH:5]=[N:6][C:7]([N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[CH2:17][O:16][C:15]3=[O:24])[CH2:10][CH2:9]2)=[C:2]([Cl:1])[CH:3]=1)=[O:26])[C:43]#[N:42]
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Komponenten

7

Edukt 5

HCID 6228DimethylformamideHCID 13387N-methyl-2-pyrrolidoneHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 226445845-Chloro-6-[4-(2-oxo-2h-3,1-benzoxazin-1(4h)-yl)piperidin-1-yl]pyridine-3-carboxylic acid

Produkt 1

HCID 22644626
N-(2-Amino-1-cyano-2-oxoethyl)-5-chloro-6-[4-(2-oxo-2H-3,1-benzoxazin-1(4H)-yl)piperidin-1-yl]pyridine-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The product of example 148 step (i) (0.14 g) was stirred as a suspension in dichloromethane (4 ml) and to this mixture was added oxalyl chloride (0.05 g) followed by N,N-dimethylformamide (0.01 g). After stirring for 1 h at room temperature the mixture was treated with 2-aminocyanoacetanide (0.14 g) 1-methyl-2-pyrrolidinone (3 ml) and then N,N-diisopropylethylamine (1 ml), stirring was then continued for a further 18 h at room temperature. The reaction mixture was partitioned between aqueous sodium bicarbonate and ethyl acetate, the organic layer was washed with water, dried and evaporated under reduced pressure. Purification was by chromatography eluting with 25% ethyl acetate/isohexane. Yield 0.09 g as a solid.

Aufarbeitung

  1. waitwas then continued for a further 18 h at room temperature
  2. customThe reaction mixture was partitioned between aqueous sodium bicarbonate and ethyl acetate
  3. washthe organic layer was washed with water
  4. customdried
  5. customevaporated under reduced pressure
  6. customPurification
  7. washeluting with 25% ethyl acetate/isohexane

Quellen und Nachweise

ORD-Eintrag
ord-e81565842d6f45cb973086b00fe0a1d1
Quelldatensatz
uspto-grants-2004_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06812226B2

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