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

HRID 1673145
ノート
印刷プレビュー

反応式

HRID 1673145 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒
HCID 6228
Dimethylformamide
溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-2fe37a1f41394aca875be80c8390741f
出典データセット
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07999117B2

反応ノート

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