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1,1'-Carbonyldiimidazole → 2-(4-[1,3]-Dioxolan-2-ylmethylphenyl)-1H-benzimidazole-4-carboxamide

HRID 1673145
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HRID 1673145 반응식
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](O)=O)=[CH:9][CH:8]=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[CH2:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]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)=[CH:9][CH:8]=1
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참가 물질

6

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 247269914-(1,3-Dioxolan-2-ylmethyl)benzoic acidHCID 534228072,3-Diaminobenzamide dihydrochloride

생성물 1

HCID 673532482-(4-[1,3]-Dioxolan-2-ylmethylphenyl)-1H-benzimidazole-4-carboxamide

시약·촉매·용매 2

HCID 1049Pyridine용매
HCID 6228
Dimethylformamide
용매

실험 절차

A solution of 4-(1,3-dioxolan-2-ylmethyl)benzoic acid (1.0 g, 4.80 mmol) in pyridine (5 mL) and N,N-dimethylformamide (5 mL) was treated with 1,1′-carbonyldiimidazole (0.856 g, 5.28 mmol) at 45° C. for 2 hours. 2,3-Diaminobenzamide dihydrochloride (synthesized as described in U.S. Pat. No. 6,737,421, column 11, EXAMPLE 2, step (e), 1.08 g, 4.80 mmol) was added and the mixture stirred at ambient temperature overnight. The mixture was concentrated and the residue heated in acetic acid (30 mL) at 80° C. for 3 hours. After cooling, the mixture was concentrated and the residue partitioned between ethyl acetate and sodium bicarbonate solution. After filtering, the filtrate was concentrated and the residue purified by flash chromatography on silica gel (0-15% methanol in 2:1 ethyl acetate/hexane) to give 1.14 g of the title compound. MS (DCI) m/z 324 (M+H)+.

후처리

  1. addition6,737,421, column 11, EXAMPLE 2, step (e), 1.08 g, 4.80 mmol) was added
  2. concentrationThe mixture was concentrated
  3. temperaturethe residue heated in acetic acid (30 mL) at 80° C. for 3 hours
  4. temperatureAfter cooling
  5. concentrationthe mixture was concentrated
  6. customthe residue partitioned between ethyl acetate and sodium bicarbonate solution
  7. filtrationAfter filtering
  8. concentrationthe filtrate was concentrated
  9. customthe residue purified by flash chromatography on silica gel (0-15% methanol in 2:1 ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-2fe37a1f41394aca875be80c8390741f
출처 데이터셋
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07999117B2

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