Sodium thiocyanate → 1-(3-Fluoro-4-(pyrrolo[2,1-f][1,2,4]triazin-4-yloxy)phenyl)-3-(2-(4-fluorophenyl)-acetyl)thiourea

HRID 2117088Notes

Reaction equation

HRID 2117088 reaction equation
[S-:1][C:2]#[N:3].[Na+].[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13](Cl)=[O:14])=[CH:8][CH:7]=1.[F:16][C:17]1[CH:18]=[C:19]([NH2:33])[CH:20]=[CH:21][C:22]=1[O:23][C:24]1[C:29]2=[CH:30][CH:31]=[CH:32][N:28]2[N:27]=[CH:26][N:25]=1>C(OCC)(=O)C.ClCCl>[F:16][C:17]1[CH:18]=[C:19]([NH:33][C:2]([NH:3][C:13](=[O:14])[CH2:12][C:9]2[CH:10]=[CH:11][C:6]([F:5])=[CH:7][CH:8]=2)=[S:1])[CH:20]=[CH:21][C:22]=1[O:23][C:24]1[C:29]2=[CH:30][CH:31]=[CH:32][N:28]2[N:27]=[CH:26][N:25]=1

Participants

6

Reactant 3

HCID 516871Sodium thiocyanateHCID 37449884-Fluorophenylacetyl chlorideHCID 210816213-Fluoro-4-(pyrrolo[2,1-f][1,2,4]triazin-4-yloxy)benzenamine2×

Product 1

HCID 116478491-(3-Fluoro-4-(pyrrolo[2,1-f][1,2,4]triazin-4-yloxy)phenyl)-3-(2-(4-fluorophenyl)-acetyl)thioureaYield 83.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a homogeneous solution of sodium thiocyanate (21 mg, 0.26 mmol) in ethyl acetate (1 mL), at room temperature under a nitrogen atmosphere, was added 4-fluorophenyl-acetyl chloride (28 μL, 0.20 mmol). The mixture was stirred for 30 minutes before being added directly to a homogeneous solution of 3-fluoro-4-(pyrrolo[2,1-f][1,2,4]-triazin-4-yloxy)benzenamine (37 mg, 0.15 mmol, Compound C of Example 22) in anhydrous dichloromethane (3 mL), under a nitrogen atmosphere. The mixture was stirred at ambient temperature for 4 h before being concentrated in vacuo. Purification by silica gel (Merck KGaA, 230-400 mesh particle size) flash chromatography, eluting with chloroform, afforded the title compound (55 mg, 83%).

Workup

  1. stirringThe mixture was stirred at ambient temperature for 4 h
  2. concentrationbefore being concentrated in vacuo
  3. customPurification by silica gel (Merck KGaA, 230-400 mesh particle size) flash chromatography
  4. washeluting with chloroform

Sources & evidence

ORD record
ord-feec08752fc8473cb7950d040268ec3d
Source dataset
uspto-grants-2008_10
Patent number
US07439246B2

Reaction notes

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