2,5-Pyridinediamine → Methyl 3-((6-aminopyridin-3-yl)carbamoyl)-4-methylbenzoate

HRID 453387Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 453387
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([CH3:14])=[C:9]([CH:13]=1)[C:10]([OH:12])=O)=[O:4].CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.CN(C)CCCN=C=NCC.[NH2:46][C:47]1[CH:52]=[CH:51][C:50]([NH2:53])=[CH:49][N:48]=1>ClCCl>[NH2:46][C:47]1[N:48]=[CH:49][C:50]([NH:53][C:10]([C:9]2[CH:13]=[C:5]([CH:6]=[CH:7][C:8]=2[CH3:14])[C:3]([O:2][CH3:1])=[O:4])=[O:12])=[CH:51][CH:52]=1

Komponenten

7

Edukt 5

HCID 203142,5-PyridinediamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 229994865-(Methoxycarbonyl)-2-methylbenzoic acid

Produkt 1

HCID 68453452Methyl 3-((6-aminopyridin-3-yl)carbamoyl)-4-methylbenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In a round-bottomed flask was charged 5-(methoxycarbonyl)-2-methylbenzoic acid (0.2 g, 1.0 mmol), dicloromethane (3 ml), n,n-diisopropylethylamine (0.7 ml, 4.0 mmol), HOBt (0.16 g, 1.2 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.24 g, 1.2 mmol), and 2,5-diaminopyridine (0.11 g, 1.0 mmol) in that order. The reaction mixture was stirred at RT under N2 for 18 h. The reaction was partitioned between DCM (30 ml) and brine (20 mL). The aqueous layer was back extracted with DCM (3×15 mL) and the combined DCM layer was dried (Na2SO4) and concentrated. The crude product was dissolved in MeOH and absorbed on silica gel, pyrified by chromatography through a Redi-Sep 40 g column, eluting with a gradient of 0% to 10% MeOH in CH2Cl2, to provide methyl 3-((6-aminopyridin-3-yl)carbamoyl)-4-methylbenzoate as a tan solid. MS (ESI, pos. ion) m/z: 286.2 (M+1).

Aufarbeitung

  1. customThe reaction was partitioned between DCM (30 ml) and brine (20 mL)
  2. extractionThe aqueous layer was back extracted with DCM (3×15 mL)
  3. dry with materialthe combined DCM layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. dissolutionThe crude product was dissolved in MeOH
  6. customabsorbed on silica gel
  7. washeluting with a gradient of 0% to 10% MeOH in CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-de5888cc3dfe4f2991bdaf9e33e27356
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492404B2

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