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

HRID 1673149노트

반응식

HRID 1673149 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 17D (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 was stirred in acetic acid (10 mL) at 80° C. overnight. After concentration, the residue was purified by flash chromatography on silica gel (ethyl acetate) to give 500 mg (22%) of the title compound. 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 residue was stirred in acetic acid (10 mL) at 80° C. overnight
  4. concentrationAfter concentration
  5. customthe residue was purified by flash chromatography on silica gel (ethyl acetate)

출처 및 근거

ORD 기록
ord-691370e5d1e24499b70660eb9baba27e
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07999117B2

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