Iodoacetamide → HCID 44415988, compound

HRID 1289945Notes

Reaction equation

HRID 1289945 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:4]=[C:5]([CH2:13][O:14][CH:15]2[CH2:19][CH2:18][CH:17]([NH:20][CH3:21])[CH:16]2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.I[CH2:31][C:32]([NH2:34])=[O:33].CCN(C(C)C)C(C)C>C(#N)C>[F:1][C:2]([F:28])([F:29])[C:3]1[CH:4]=[C:5]([CH2:13][O:14][CH:15]2[CH2:19][CH2:18][CH:17]([N:20]([CH2:31][C:32]([NH2:34])=[O:33])[CH3:21])[CH:16]2[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

5

Reactant 3

HCID 3727IodoacetamideHCID 81531DiisopropylethylamineHCID 75024269HCID 75024269, compound

Product 1

HCID 44415988HCID 44415988, compoundYield 123.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 50 mg of amine prepared in Example 11, 33 mg of iodoacetamide and 0.05 mL of DIPEA in 0.5 mL of acetonitrile was heated in a sealed vial at 50° C. for 2 h (or room temperature for 16 h). The volatiles were evaporated under a stream of nitrogen and the residue was purified on a 1 mm preparative silica gel plate eluted with 5% MeOH in methylene chloride to afford 70 mg of title compound. Mass spec (NH3 /CI): 475 (M+1).

Workup

  1. customThe volatiles were evaporated under a stream of nitrogen
  2. customthe residue was purified on a 1 mm preparative silica gel plate
  3. washeluted with 5% MeOH in methylene chloride

Sources & evidence

ORD record
ord-312fc7ca520c4272950303a67197ca16
Source dataset
uspto-grants-1998_05
Patent number
US05750549

Reaction notes

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