1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → Methyl 2,6-difluoro-4-[(3-methoxymethoxy-5,5,8,8,-tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-benzoate

HRID 1935654Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1935654
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:6]([C:19](O)=[O:20])=[CH:7][C:8]2[C:9]([CH3:18])([CH3:17])[CH2:10][CH2:11][C:12]([CH3:16])([CH3:15])[C:13]=2[CH:14]=1.[F:22][C:23]1[CH:32]=[C:31]([NH2:33])[CH:30]=[C:29]([F:34])[C:24]=1[C:25]([O:27][CH3:28])=[O:26].Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[F:22][C:23]1[CH:32]=[C:31]([NH:33][C:19]([C:6]2[C:5]([O:4][CH2:3][O:2][CH3:1])=[CH:14][C:13]3[C:12]([CH3:16])([CH3:15])[CH2:11][CH2:10][C:9]([CH3:18])([CH3:17])[C:8]=3[CH:7]=2)=[O:20])[CH:30]=[C:29]([F:34])[C:24]=1[C:25]([O:27][CH3:28])=[O:26]

Komponenten

6

Edukt 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 158405323-(Methoxymethoxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carboxylic acidHCID 23001755Methyl 4-amino-2,6-difluorobenzoate

Produkt 1

HCID 22465055Methyl 2,6-difluoro-4-[(3-methoxymethoxy-5,5,8,8,-tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 3-methoxymethoxy-5,5,8,8,-tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid (Compound K, as described in U.S. Pat. No. 5,856,490, 112mg, 0.38 mmol) in 6 ml of anhydrous methylene chloride was added 4-(dimethylamino)pyridine (DMAP, 100 mg, 0.46mmol), methyl 2,6-difluoro-4-aminobenzoate (Compound H1, as described in U.S. Pat. No. 5,856,490, 77mg, 0.38mmol ) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC, 110 mg, 0.57 mmol). The reaction mixture was stirred at room temperature for overnight then concentrated to dryness. The residue was purified by column chromatography with ethyl acetate: hexane (1:9) to yield the title compound as a clear oil.

Aufarbeitung

  1. concentrationthen concentrated to dryness
  2. customThe residue was purified by column chromatography with ethyl acetate: hexane (1:9)

Quellen und Nachweise

ORD-Eintrag
ord-da1dd56b9f354d9ca2f8683bc6214c71
Quelldatensatz
uspto-grants-2002_05
Patentnummer
US06387950B2

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