Triethylamine → N-methoxy-N,1-dimethyl-1H-benzo[d]imidazole-5-carboxamide

HRID 626242

Reaktionsgleichung

Reaktionsgleichung von HRID 626242
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([OH:13])=O)=[CH:10][C:5]=2[N:4]=[CH:3]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.[CH3:36][O:37][NH:38][CH3:39].CCN(CC)CC>C(Cl)Cl.O>[CH3:36][O:37][N:38]([CH3:39])[C:11]([C:9]1[CH:8]=[CH:7][C:6]2[N:2]([CH3:1])[CH:3]=[N:4][C:5]=2[CH:10]=1)=[O:13]

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 49130631-Methyl-1H-benzimidazole-5-carboxylic acid

Produkt 1

HCID 86665700N-methoxy-N,1-dimethyl-1H-benzo[d]imidazole-5-carboxamideAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A suspension of 1-methyl-1H-benzo[d]imidazole-5-carboxylic acid (9.7 g, 1.0 eq), EDCI (10.5 g, 1.2 eq), and HOBt (7.4 g, 1.2 eq) in 150 mL CH2Cl2 was stirred at rt for 5 min, and then N-methoxymethanamine hydrochloride (6.7 g, 1.5 eq) and Et3N (18.5 g, 4.0 eq) were added. The reaction mixture was stirred at rt overnight. Water was added and extracted with CH2Cl2. The extract was dried, concentrated, and purified by column chromatography to give the desired product (9.5 g, 80%). 1H NMR (400 MHz, CDCl3) δ 8.20 (d, J=1.2 Hz, 1H), 7.93 (s, 1H), 7.72 (dd, J=8.8 Hz, 1.6 Hz, 1H), 7.40 (dd, J=8.4 Hz, 0.8 Hz, 1H), 3.87 (s, 3H), 3.57 (s, 3H), 3.40 (s, 3H).

Aufarbeitung

  1. stirringThe reaction mixture was stirred at rt overnight
  2. extractionextracted with CH2Cl2
  3. customThe extract was dried
  4. concentrationconcentrated
  5. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8cdf096c8eec4819ac754e6c42a6c534
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309211B2

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