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Sodium Iodide → 3-[(3-{4-[5-Acetyl-1-(3-fluoropropyl)-1H-pyrrol-3-yl]-2-amino-1-methyl-5-oxo-4,5-dihydro-1H-imidazol-4-yl}phenoxy)methyl]benzamide

HRID 2220475
Notes
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Reaction equation

HRID 2220475 reaction equation
[C:1]([C:4]1[N:8]([CH2:9][CH2:10][CH2:11][F:12])[CH:7]=[C:6]([C:13]2([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=3)[N:17]=[C:16]([NH2:18])[N:15]([CH3:19])[C:14]2=[O:20])[CH:5]=1)(=[O:3])[CH3:2].Cl[CH2:29][C:30]1[CH:31]=[C:32]([CH:36]=[CH:37][CH:38]=1)[C:33]([NH2:35])=[O:34].[I-].[Na+].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C>[C:1]([C:4]1[N:8]([CH2:9][CH2:10][CH2:11][F:12])[CH:7]=[C:6]([C:13]2([C:21]3[CH:22]=[C:23]([CH:24]=[CH:25][CH:26]=3)[O:27][CH2:29][C:30]3[CH:31]=[C:32]([CH:36]=[CH:37][CH:38]=3)[C:33]([NH2:35])=[O:34])[C:14](=[O:20])[N:15]([CH3:19])[C:16]([NH2:18])=[N:17]2)[CH:5]=1)(=[O:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 7371453-Chloromethyl-benzamideHCID 597726545-[5-acetyl-1-(3-fluoropropyl)-1H-pyrrol-3-yl]-2-amino-5-(3-hydroxyphenyl)-3-methyl-3,5-dihydro-4H-imidazol-4-one

Product 1

HCID 597727593-[(3-{4-[5-Acetyl-1-(3-fluoropropyl)-1H-pyrrol-3-yl]-2-amino-1-methyl-5-oxo-4,5-dihydro-1H-imidazol-4-yl}phenoxy)methyl]benzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 5-[5-acetyl-1-(3-fluoropropyl)-1H-pyrrol-3-yl]-2-amino-5-(3-hydroxyphenyl)-3-methyl-3,5-dihydro-4H-imidazol-4-one, 3-(chloromethyl)benzamide, sodium iodide, and cesium carbonate in dimethylformamide was heated to 45° C. for 16 hours. The cooled reaction mixture was poured into ethyl acetate and washed with water. The organic phase was dried over sodium sulfate and evaporated. The resultant residue was purified by HPLC using a CN bonded phase preparative column and by precipitation from hexane to give the title product as a white solid, identified by NMR and mass spectral analyses.

Workup

  1. customThe cooled reaction mixture
  2. washwashed with water
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customevaporated
  5. customThe resultant residue was purified by HPLC
  6. customby precipitation from hexane

Sources & evidence

ORD record
ord-197137909d54496ca9b52a5371aaed4a
Source dataset
uspto-grants-2008_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07417047B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes