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

HRID 626242

반응식

HRID 626242 반응식
[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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8cdf096c8eec4819ac754e6c42a6c534
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309211B2

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