Hydrochloric Acid → 4-(1h-Imidazol-2-ylcarbamoyl)-1h-benzoimidazole-2-carboxylic acid

HRID 1910136ノート

反応式

HRID 1910136 の反応式
[NH2:1][C:2]1[C:15]([NH2:16])=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([NH:6][C:7]1[NH:8][CH:9]=[CH:10][N:11]=1)=[O:5].Cl[C:18](Cl)(Cl)[C:19](N)=[O:20].Cl.[Li+].[OH-:26]>C(O)(=O)C.CO.C1COCC1>[NH:11]1[CH:10]=[CH:9][N:8]=[C:7]1[NH:6][C:4]([C:3]1[C:2]2[N:1]=[C:18]([C:19]([OH:20])=[O:26])[NH:16][C:15]=2[CH:14]=[CH:13][CH:12]=1)=[O:5]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 61144TrichloroacetamideHCID 669405262,3-Diamino-n-(1h-imidazol-2-yl)-benzamide

生成物 1

HCID 669403914-(1h-Imidazol-2-ylcarbamoyl)-1h-benzoimidazole-2-carboxylic acid収率 40%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirring solution of 200 mg (0.92 mmol) of 2,3-diamino-N-(1H-imidazol-2-yl)-benzamide (synthesized as described in Intermediate-B) in 2.0 mL of acetic acid was added 200 mg (1.15 mmol) of 2,2,2-trichloroacetamide and stirring continued for 30 min at r.t. Then 0.5 mL of 1% HCl in methanol was added and stirred for another 45 min at r.t. Evaporation of the solvent gave the crude ester, which was dissolved in 4:1 THF and methanol (5 mL) and then 1.0 mL of 2N LiOH was added at r.t. The reaction mixture was stirred at r.t. for 30 min, the pH was adjusted to 3.0 and then extracted with ethyl acetate twice (2×25 mL). The combined organic solvents were dried, evaporated to provide 100 mg (40%) of 4-(1H-imidazol-2-ylcarbamoyl)-1H-benzoimidazole-2-carboxylic acid, which was used, for the next step without further purification. LCMS: 272 (M+1)+.

後処理

  1. stirringstirred for another 45 min at r.t
  2. customEvaporation of the solvent
  3. customgave the crude ester, which
  4. stirringThe reaction mixture was stirred at r.t. for 30 min
  5. extractionextracted with ethyl acetate twice (2×25 mL)
  6. customThe combined organic solvents were dried
  7. customevaporated

出典と根拠

ORDレコード
ord-a0ca6bcd64f5498f8ff05e43a78307ff
出典データセット
uspto-grants-2013_12
特許番号
US08598353B2

反応ノート

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