Water → HCID 58975972, compound

HRID 601053Notes

Reaction equation

HRID 601053 reaction equation
[F:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([NH2:14])=[N:12][C:11]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[CH:18][CH:17]=2)=[N:10]1.[Cu][C:29]#[N:30].O>CN(P(N(C)C)(N(C)C)=O)C>[NH2:14][C:13]1[N:9]([C:3]2[CH:4]=[CH:5][C:6]([C:29]#[N:30])=[CH:7][C:2]=2[F:1])[N:10]=[C:11]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[CH:18][CH:17]=2)[N:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 58976773HCID 58976773, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 58975972HCID 58975972, compoundYield 10.6%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 1-(2-fluoro-4-iodo-phenyl)-N3-(4-morpholino-phenyl)-1H-[1,2,4]triazole-3,5-diamine (0.48 g, 0.99 mmol) and copper (I) cyanide (0.09 g, 0.99 mmol) in HMPA (3 mL) was heated at 55° C. for 2 h, then poured into water (75 mL) and filtered, washing with water. The filter cake was suspended in chloroform (100 mL) and methanol (5 mL), was refluxed for 2 h, cooled, filtered and evaporated. Purification by semi-preparative HPLC provided the title compound (0.04 g, 9% yield) as a pale tan lyophilate.

Workup

  1. filtrationfiltered
  2. washwashing with water
  3. temperaturemethanol (5 mL), was refluxed for 2 h
  4. temperaturecooled
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by semi-preparative HPLC

Sources & evidence

ORD record
ord-b7a9544aa61d4fb29cf78c12a1f9e1a7
Source dataset
uspto-grants-2011_03
Patent number
US07902239B2

Reaction notes

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