2-Fluorophenyl isothiocyanate → HCID 11703665, compound

HRID 1713728Notes

Reaction equation

HRID 1713728 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]=[C:9]=S.[NH:11]([C:13](=[O:29])[C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[CH:19][CH:18]=1)=[O:15])[NH2:12].N=C=N>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:29][C:13]([C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)=[CH:19][CH:18]=2)=[O:15])=[N:11][N:12]=1

Participants

5

Reactant 3

HCID 975202-Fluorophenyl isothiocyanateHCID 160435CarbodiimideHCID 59464167HCID 59464167, compound2×

Product 1

HCID 11703665HCID 11703665, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

2-Fluorophenylisothiocyanate (92 μL, 0.75 mmol) was added to a stirred suspension of 2-hydrazino-N-(4-morpholin-4-ylphenyl)-2-oxoacetamide (Intermediate 16, 160 mg, 0.6 mmol) in DMF (10 mL) and stirred at 50° C. until a clear solution was obtained. PS-Carbodiimide (909 mg, 1.2 mmol) was added and the reaction was heated at 80° C. for a further 4 h. The reaction was filtered and the resin washed with DMF (5 mL). The combined DMF solutions were concentrated in vacuo and the residue triturated with diethyl ether to give the title compound as a yellow powder (190 mg, 82%):

Workup

  1. customwas obtained
  2. temperaturethe reaction was heated at 80° C. for a further 4 h
  3. filtrationThe reaction was filtered
  4. washthe resin washed with DMF (5 mL)
  5. concentrationThe combined DMF solutions were concentrated in vacuo
  6. customthe residue triturated with diethyl ether

Sources & evidence

ORD record
ord-8fa05ea104204d11b06a77c36d9cb99c
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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