Acetic Acid → HCID 18616879、化合物

HRID 1263538

反応式

HRID 1263538 の反応式
[N+:1]([C:4]1[C:5]([NH2:11])=[C:6]([NH2:10])[CH:7]=[CH:8][CH:9]=1)([O-])=O.[CH3:12][C:13]1[C:14]([NH2:20])=[C:15]([NH2:19])[CH:16]=[CH:17][CH:18]=1.[ClH:21].Cl.[C:23](=N)(OCC)[CH2:24][C:25](=N)OCC.C(O)(=O)C>Cl>[ClH:21].[ClH:21].[CH3:12][C:13]1[C:14]2[N:20]=[C:23]([CH2:24][C:25]3[NH:1][C:4]4[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[C:5]=4[N:11]=3)[NH:19][C:15]=2[CH:16]=[CH:17][CH:18]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 175932,3-DiaminotolueneHCID 73106Diethyl malonimidateHCID 43595253-Nitro-1,2-phenylenediamine

生成物 1

HCID 18616879HCID 18616879、化合物収率 66.6%

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

実験手順

The following components were reacted according to General Procedure 1, above: 3-nitro-1,2-phenylenediamine (0.5 g; 3.26 mmoles), 3-methyl-1,2-phenylenediamine (0.4 g; 3.26 mmoles), diethyl malonimidate dihydrochloride (1.1 eq.; 0.83 g; 3.60 mmoles) and acetic acid (25 mL). The crude mixture of three compounds was then reduced according to General Procedure 2, above. The crude solid product was taken up in 10 mL of dilute HCl, purified by preparative HPLC (15 to 75% acetonitrile (with 0.1% TFA) over 60 minutes) and converted to the HCl salt by three freeze drying cycles with dilute HCl. This procedure gave 0.42 g of pure 2-[(4-methyl-1H-benzimidazol-2-yl)methyl]-1H-benzimidazol-4-ylamine dihydrochloride in 37% yield. It had MS: m/z=278.2 [N+1] amu and gave one peak on HPLC at both 210 and 280 nm (12.01 minutes using the JWTFACN gradient).

後処理

  1. customThe following components were reacted
  2. additionThe crude mixture of three compounds
  3. custompurified by preparative HPLC (15 to 75% acetonitrile (with 0.1% TFA) over 60 minutes)
  4. dry with materialdrying cycles with dilute HCl

出典と根拠

ORDレコード
ord-3409410321724b4ba1a2df2c75a03243
出典データセット
uspto-grants-2003_04
特許番号
US06541486B1

関連ノート

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