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

HRID 2374685노트

반응식

HRID 2374685 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6228Dimethylformamide용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-0941408ce7024a47a935ba4d6ca7afc6
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07462724B2

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