Triethylamine → HCID 60491075, Verbindung

HRID 2272969

Reaktionsgleichung

Reaktionsgleichung von HRID 2272969
[C:1]([N:5]1[CH:9]=[C:8]([C:10]([OH:12])=O)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:14][NH:15][O:16][CH3:17].Cl.CN(C)CCCN=C=NCC.OS1C2C=CC=CC=2N=C1.C(N(CC)CC)C>ClCCl>[CH3:17][O:16][N:15]([CH3:14])[C:10]([C:8]1[CH:7]=[N:6][N:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:9]=1)=[O:12]

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 246962911-tert-Butyl-1H-pyrazole-4-carboxylic acidHCID 178527226HCID 178527226, Verbindung

Produkt 1

HCID 60491075HCID 60491075, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of 5.00 g (29.7 mmol) 1-tert-butyl-1H-pyrazole-4-carboxylic acid and 5.80 g (59.5 mmol) N,O-dimethylhydroxylamine hydrochloride in 60 ml dichloromethane are added 12.5 g (65.4 mmol) N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride, 4.42 g (32.7 mmol) 1-hydroxybenzothiazol and 16.5 ml (119 mmol) triethylamine. The reaction mixture is stirred for 18 hours at room temperature. It is quenched with saturated sodium hydrogen carbonate solution and the mixture is partitioned between water and dichloromethane. The organic phase is dried over sodium sulfate and evaporated. The residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent to afford 1-tert-butyl-1H-pyrazole-4-carboxylic acid methoxy-methyl-amide as colorless crystals; HPLC/MS 1.91 min (B), [M+H] 212.

Aufarbeitung

  1. customIt is quenched with saturated sodium hydrogen carbonate solution
  2. customthe mixture is partitioned between water and dichloromethane
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customevaporated
  5. customThe residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent

Quellen und Nachweise

ORD-Eintrag
ord-ea6b68daf65d4710bf6eec751004ee32
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09120805B2

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