HCID 2774522, compound → HCID 58976773, compound

HRID 601041Notes

Reaction equation

HRID 601041 reaction equation
[C:1]([NH:3][C:4](=[N:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[CH:15][CH:14]=1)OC1C=CC=CC=1)#[N:2].[F:25][C:26]1[CH:31]=[C:30]([I:32])[CH:29]=[CH:28][C:27]=1[NH:33][NH2:34]>C(N)(=O)C.C(OCC)(=O)C>[F:25][C:26]1[CH:31]=[C:30]([I:32])[CH:29]=[CH:28][C:27]=1[N:33]1[C:1]([NH2:2])=[N:3][C:4]([NH:12][C:13]2[CH:14]=[CH:15][C:16]([N:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)=[CH:17][CH:18]=2)=[N:34]1

Participants

5

Reactant 2

HCID 2774522HCID 2774522, compoundHCID 58976101HCID 58976101, compound

Product 1

HCID 58976773HCID 58976773, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 178AcetamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of N-cyano-N′-(4-morpholino-phenyl)-O-phenylisourea (0.69 g, 2.14 mmol) and 2-fluoro-4-iodo-phenylhydrazine (0.65 g, 2.57 mmol) in dimetheyl acetamide (4 mL) was heated at 120° C. for 24 h. The reaction is diluted with ethyl acetate, washed with water (3 times) and brine, dried (sodium sulfate) and evaporated. Purification by flash chromatography (SiO2) eluted with 4:96 methanol:dichloromethane, followed by semi-preparative HPLC provided the title compound (0.03 g, 5% yield) as a white lyophilate.

Workup

  1. washwashed with water (3 times) and brine
  2. dry with materialdried (sodium sulfate)
  3. customevaporated
  4. customPurification by flash chromatography (SiO2)
  5. washeluted with 4:96 methanol

Sources & evidence

ORD record
ord-77415cdc871648b6ac3d24c512951ef6
Source dataset
uspto-grants-2011_03
Patent number
US07902239B2

Reaction notes

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