Triethylamine → 5-(4-Fluoro-phenoxy)-2-pyridin-2-yl-6-(1-pyrimidin-2-yl-pyrrolidin-2-yl)-1H-benzimidazole

HRID 13281

Reaction equation

HRID 13281 reaction equation
C(N(CC)CC)C.Cl[C:9]1[N:14]=[CH:13][CH:12]=[CH:11][N:10]=1.[F:15][C:16]1[CH:42]=[CH:41][C:19]([O:20][C:21]2[C:35]([CH:36]3[CH2:40][CH2:39][CH2:38][NH:37]3)=[CH:34][C:24]3[NH:25][C:26]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=4)=[N:27][C:23]=3[CH:22]=2)=[CH:18][CH:17]=1>C(O)C>[F:15][C:16]1[CH:17]=[CH:18][C:19]([O:20][C:21]2[C:35]([CH:36]3[CH2:40][CH2:39][CH2:38][N:37]3[C:9]3[N:14]=[CH:13][CH:12]=[CH:11][N:10]=3)=[CH:34][C:24]3[NH:25][C:26]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=4)=[N:27][C:23]=3[CH:22]=2)=[CH:41][CH:42]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 744042-ChloropyrimidineHCID 231455755-(4-fluoro-phenoxy)-2-pyridin-2-yl-6-pyrrolidin-2-yl-1H-benzimidazole

Product 1

HCID 231454735-(4-Fluoro-phenoxy)-2-pyridin-2-yl-6-(1-pyrimidin-2-yl-pyrrolidin-2-yl)-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.013 ml of triethylamine and 6.3 mg of 2-chloro-pyrimidine were added in order to an ethanol (2 ml) solution of 17.1 mg of 5-(4-fluoro-phenoxy)-2-pyridin-2-yl-6-pyrrolidin-2-yl-1H-benzimidazole obtained in Example 168, and the reaction liquid was heated under reflux for 3 hours. The reaction solvent was evaporated away under reduced pressure, and the resulting residue was purified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid], and the resulting fraction was diluted with ethyl acetate, washed with aqueous saturated sodium bicarbonate and saturated saline in order, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure to obtain the entitled compound as a white solid.

Workup

  1. customthe reaction liquid
  2. temperaturewas heated
  3. temperatureunder reflux for 3 hours
  4. customThe reaction solvent was evaporated away under reduced pressure
  5. customthe resulting residue was purified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid]
  6. additionthe resulting fraction was diluted with ethyl acetate
  7. washwashed with aqueous saturated sodium bicarbonate and saturated saline in order
  8. dry with materialdried with anhydrous sodium sulfate
  9. customThe solvent was evaporated away under reduced pressure

Sources & evidence

ORD record
ord-1f00ef826a5e4bb395bbf8e1102e086d
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Linked notes

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