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Iodoacetamide → 2-(2-(6-(4-Fluoro-phenoxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-acetamide

HRID 13282
Notes
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Reaction equation

HRID 13282 reaction equation
C(=O)([O-])[O-].[K+].[K+].I[CH2:8][C:9]([NH2:11])=[O:10].[F:12][C:13]1[CH:39]=[CH:38][C:16]([O:17][C:18]2[C:32]([CH:33]3[CH2:37][CH2:36][CH2:35][NH:34]3)=[CH:31][C:21]3[NH:22][C:23]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=4)=[N:24][C:20]=3[CH:19]=2)=[CH:15][CH:14]=1>C(#N)C>[F:12][C:13]1[CH:14]=[CH:15][C:16]([O:17][C:18]2[C:32]([CH:33]3[CH2:37][CH2:36][CH2:35][N:34]3[CH2:8][C:9]([NH2:11])=[O:10])=[CH:31][C:21]3[NH:22][C:23]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=4)=[N:24][C:20]=3[CH:19]=2)=[CH:38][CH:39]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 3727IodoacetamideHCID 11430Potassium CarbonateHCID 231455755-(4-fluoro-phenoxy)-2-pyridin-2-yl-6-pyrrolidin-2-yl-1H-benzimidazole

Product 1

HCID 231451242-(2-(6-(4-Fluoro-phenoxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-acetamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

11.4 mg of potassium carbonate and 11.1 mg of iodoacetamide were added in order to an acetonitrile (1 ml) solution of 20 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 stirred overnight at room temperature. The reaction liquid was concentrated, 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. customThe reaction liquid
  3. concentrationwas concentrated
  4. 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]
  5. additionthe resulting fraction was diluted with ethyl acetate
  6. washwashed with aqueous saturated sodium bicarbonate and saturated saline in order
  7. dry with materialdried with anhydrous sodium sulfate
  8. customThe solvent was evaporated away under reduced pressure

Sources & evidence

ORD record
ord-82f3e1f2420e4be1992565f49031ff26
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07728025B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes