1-Hydroxybenzotriazole → 2,6-Diamino-N-(5-benzyl-thiophen-2-ylmethyl)-nicotinamide

HRID 2080186Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2080186
[NH2:1][C:2]1[N:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[CH2:34]([C:41]1[S:45][C:44]([CH2:46][NH2:47])=[CH:43][CH:42]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>CS(C)=O.[Cl-].[Na+].O>[NH2:1][C:2]1[N:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH:47][CH2:46][C:44]1[S:45][C:41]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:42][CH:43]=1)=[O:6]

Komponenten

7

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 189772452,6-Diaminonicotinic acidHCID 231306122-Thiophenemethanamine,5-(phenylmethyl)-

Produkt 1

HCID 231303582,6-Diamino-N-(5-benzyl-thiophen-2-ylmethyl)-nicotinamideAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a solution of 2,6-diaminonicotinic acid described in Preparation Example A-15 (173 mg, 1.13 mmol) in dimethylsulfoxide (15 mL) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (433 mg, 2.26 mmol), 1-hydroxybenzotriazole (346 mg, 2.26 mmol) and C-(5-benzyl-thiophen-2-yl)-methylamine described in Preparation Example 42 (230 mg, 1.13 mmol), and the solution was stirred at room temperature fro 16 hours 30 minutes. The reaction solution was poured into brine, the solution was extracted with ethyl acetate, the organic layer was dried over anhydrous magnesium sulfate and then concentrated. The obtained residue was subjected to NH silica gel column chromatography, eluted with solvent (ethyl acetate) and the title compound (114 mg, 0.34 mmol, 30%) was obtained.

Aufarbeitung

  1. extractionthe solution was extracted with ethyl acetate
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. washeluted with solvent (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-66fafe050d8140739905096af590ecdc
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07932272B2

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