Triethylamine → Methyl 4-chloro-2-[(3,5-dimethylpyrazin-2-yl)amino]-1-(3-hydroxypropyl)-1h-benzimidazole-7-carboxylate

HRID 1628750Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1628750
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([NH:12][CH2:13][CH2:14][CH2:15][OH:16])[C:3]=1[NH:17][C:18](=S)[NH:19][C:20]1[C:25]([CH3:26])=[N:24][C:23]([CH3:27])=[CH:22][N:21]=1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>O1CCCC1.C(=O)([O-])O.[Na+]>[Cl:1][C:2]1[C:3]2[N:17]=[C:18]([NH:19][C:20]3[C:25]([CH3:26])=[N:24][C:23]([CH3:27])=[CH:22][N:21]=3)[N:12]([CH2:13][CH2:14][CH2:15][OH:16])[C:4]=2[C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86632931Methyl 4-chloro-3-{[(3,5-dimethylpyrazin-2-yl)carbamothioyl]amino}-2-[(3-hydroxypropyl)amino]benzoate

Produkt 1

HCID 68774496Methyl 4-chloro-2-[(3,5-dimethylpyrazin-2-yl)amino]-1-(3-hydroxypropyl)-1h-benzimidazole-7-carboxylateAusbeute 73,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of the resulting thiourea (435 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (214 mg, 1.12 mmol), and triethylamine (0.16 mL) in tetrahydrofuran (3.0 mL) was stirred at 60° C. for 2 hr. The mixture was diluted with saturated aqueous sodium hydrogen carbonate, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was washed with ethyl acetate/diisopropyl ether to give methyl 4-chloro-2-[(3,5-dimethylpyrazin-2-yl)amino]-1-(3-hydroxypropyl)-1H-benzimidazole-7-carboxylate (294 mg).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washThe residue was washed with ethyl acetate/diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-3173109b7022457995b85c45523b3ab0
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785460B2

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