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

HRID 626242

反応式

HRID 626242 の反応式
[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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8cdf096c8eec4819ac754e6c42a6c534
出典データセット
uspto-grants-2016_04
特許番号
US09309211B2

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