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

HRID 1910136노트

반응식

HRID 1910136 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 887Methanol용매2회HCID 8028Tetrahydrofuran용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-a0ca6bcd64f5498f8ff05e43a78307ff
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598353B2

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