Ethyl Acetate → 1-(3-Fluoro-4-hydroxyphenyl)-3-(2-(4-fluorophenyl)acetyl)thiourea

HRID 347456

Reaction equation

HRID 347456 reaction equation
NC1C=CC(O)=C(F)C=1.FC1C=CC(CC(SC#N)=O)=CC=1.[F:23][C:24]1[CH:25]=[C:26]([NH:43][C:44]([NH:46][C:47](=[O:56])[CH2:48][C:49]2[CH:54]=[CH:53][C:52]([F:55])=[CH:51][CH:50]=2)=[S:45])[CH:27]=[CH:28][C:29]=1[O:30]C1C2=C(C)C(OC)=CN2N=CN=1.CCOC(C)=O>C(Cl)Cl>[F:23][C:24]1[CH:25]=[C:26]([NH:43][C:44]([NH:46][C:47](=[O:56])[CH2:48][C:49]2[CH:50]=[CH:51][C:52]([F:55])=[CH:53][CH:54]=2)=[S:45])[CH:27]=[CH:28][C:29]=1[OH:30]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 2735918Phenol, 4-amino-2-fluoro-HCID 116271861-(3-Fluoro-4-(6-methoxy-5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yloxy)phenyl)-3-(2-(4-fluorophenyl)acetyl)thioureaHCID 21081546HCID 21081546, compound

Product 1

HCID 210814951-(3-Fluoro-4-hydroxyphenyl)-3-(2-(4-fluorophenyl)acetyl)thioureaYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-amino-2-fluorophenol (50 mg, 0.3 mmol, Indofine Chemical Co.) in CH2Cl2 (5 mL) was added a 0.25 M solution of 2-(4-fluorophenyl)-1-thiocyanatoethanone (prepared using a similar procedure for the synthesis of Compound A of Example 2) in EtOAc (1.6 mL, 0.4 mmol). The reaction was stirred at room temperature for 20 minutes, concentrated in vacuo and purified by silica gel flash chromatography (eluted with 1–25% EtOAc/CH2Cl2) to give the title compound (100 mg, 95%) as a white solid.

Workup

  1. customprepared
  2. concentrationconcentrated in vacuo
  3. custompurified by silica gel flash chromatography (eluted with 1–25% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-136b669c08d84bff8d58a9aded2b89e0
Source dataset
uspto-grants-2007_02
Patent number
US07173031B2

Linked notes

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