Pyridine → 2-(5-bromo-pyridin-2-yl)-5-(4-methanesulfonyl-phenoxy)-6-pyrrolidin-2-yl-1H-benzimidazole

HRID 13344

反応式

HRID 13344 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](O)=O)=[N:6][CH:7]=1.Cl.CN(C)CCCN=C=NCC.N1C=CC=CC=1.[NH2:29][C:30]1[C:35]([NH2:36])=[CH:34][C:33]([CH:37]2[CH2:41][CH2:40][CH2:39][N:38]2C(OC(C)(C)C)=O)=[C:32]([O:49][C:50]2[CH:55]=[CH:54][C:53]([S:56]([CH3:59])(=[O:58])=[O:57])=[CH:52][CH:51]=2)[CH:31]=1>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:36][C:35]3[CH:34]=[C:33]([CH:37]4[CH2:41][CH2:40][CH2:39][NH:38]4)[C:32]([O:49][C:50]4[CH:55]=[CH:54][C:53]([S:56]([CH3:59])(=[O:58])=[O:57])=[CH:52][CH:51]=4)=[CH:31][C:30]=3[N:29]=2)=[N:6][CH:7]=1

参加物

6

反応物 4

HCID 1049PyridineHCID 6085445-Bromopyridine-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23145168t-Butyl 2-(4,5-diamino-2-(4-methanesulfonyl-phenoxy)phenyl)-pyrrolidine-1-carboxylate

生成物 1

HCID 231454112-(5-bromo-pyridin-2-yl)-5-(4-methanesulfonyl-phenoxy)-6-pyrrolidin-2-yl-1H-benzimidazole

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

220 mg of 5-bromopyridine-2-carboxylic acid and 260 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide monohydrochloride were added in order to a pyridine (10 ml) solution of 500 mg of t-butyl 2-(4,5-diamino-2-(4-methanesulfonyl-phenoxy)-phenyl)-pyrrolidine-1-carboxylate, and the reaction liquid was stirred at room temperature for 12 hours. The reaction liquid was diluted with chloroform, washed with water and saturated saline in order, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, the resulting residue was dissolved in 10 ml of trifluoroacetic acid, and the reaction liquid was heated under reflux for 3 hours. After cooled, the reaction liquid was distilled under reduced pressure, and the resulting residue was diluted with chloroform, and then made basic with aqueous saturated sodium bicarbonate added thereto. Then, the organic layer was washed with saturated saline and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol/aqueous ammonia=50/1/0.1) to obtain the entitled compound as a colorless oily substance.

後処理

  1. customthe reaction liquid
  2. customThe reaction liquid
  3. washwashed with water and saturated saline in order
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe solvent was evaporated away under reduced pressure
  6. dissolutionthe resulting residue was dissolved in 10 ml of trifluoroacetic acid
  7. customthe reaction liquid
  8. temperaturewas heated
  9. temperatureunder reflux for 3 hours
  10. temperatureAfter cooled
  11. customthe reaction liquid
  12. distillationwas distilled under reduced pressure
  13. additionthe resulting residue was diluted with chloroform
  14. additionadded
  15. washThen, the organic layer was washed with saturated saline
  16. dry with materialdried with anhydrous magnesium sulfate
  17. customThe solvent was evaporated away under reduced pressure
  18. customthe resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol/aqueous ammonia=50/1/0.1)
  19. customto obtain the entitled compound as a colorless oily substance

出典と根拠

ORDレコード
ord-d64018e6e5874ab7ac823e30805ed01a
出典データセット
uspto-grants-2010_06
特許番号
US07728025B2

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