1,1'-Carbonyldiimidazole → 2-(4-[1,3] Dioxolan-2-yl-2-fluorophenyl)-1h-benzimidazole-4-carboxamide

HRID 2374685ノート

反応式

HRID 2374685 の反応式
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:14]=[CH:13][C:9]([C:10](O)=O)=[C:8]([F:15])[CH:7]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.Cl.[NH2:30][C:31]1[C:39]([NH2:40])=[CH:38][CH:37]=[CH:36][C:32]=1[C:33]([NH2:35])=[O:34]>N1C=CC=CC=1.CN(C)C=O>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:14]=[CH:13][C:9]([C:10]2[NH:40][C:39]3[CH:38]=[CH:37][CH:36]=[C:32]([C:33]([NH2:35])=[O:34])[C:31]=3[N:30]=2)=[C:8]([F:15])[CH:7]=1

参加物

6

反応物 3

HCID 682631,1'-CarbonyldiimidazoleHCID 534228072,3-Diaminobenzamide dihydrochlorideHCID 673539164-(1,3-Dioxolan-2-yl)-2-fluorobenzoic acid

生成物 1

HCID 673529522-(4-[1,3] Dioxolan-2-yl-2-fluorophenyl)-1h-benzimidazole-4-carboxamide収率 22%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of EXAMPLE 20D (1.5 g, 7.1 mmol) in pyridine (5 mL) and N,N-dimethylformamide (20 mL) was treated with 1,1′-carbonyldiimidazole (1.4 g, 8.5 mmol) at 40° C. for 30 minutes. 2,3-Diaminobenzamide dihydrochloride (synthesized as described in U.S. Pat. No. 6,737,421, column 11, EXAMPLE 2, step (e), 1.58 g, 7.1 mmol) was added and the mixture stirred at ambient temperature overnight. Solvents were removed and the residue suspended in 10 mL of acetic acid. The mixture was stirred at 80° C. overnight, cooled, and concentrated and the residue was purified by flash chromatography using ethyl acetate to give the title compound (500 mg, 22%). MS (DCI/NH3) m/z 329 (M+H)+.

後処理

  1. addition6,737,421, column 11, EXAMPLE 2, step (e), 1.58 g, 7.1 mmol) was added
  2. customSolvents were removed
  3. stirringThe mixture was stirred at 80° C. overnight
  4. temperaturecooled
  5. concentrationconcentrated
  6. customthe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-0941408ce7024a47a935ba4d6ca7afc6
出典データセット
uspto-grants-2008_12
特許番号
US07462724B2

反応ノート

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