Water → HCID 22257872, compound

HRID 1350096Notes

Reaction equation

HRID 1350096 reaction equation
[CH2:1]([NH:8][C:9](=[O:12])[CH2:10]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[F:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1.O>CN(C=O)C>[CH2:1]([NH:8][C:9](=[O:12])[CH2:10][NH:27][C:26]1[CH:28]=[CH:29][C:23]([F:22])=[CH:24][CH:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 97314-FluoroanilineHCID 81531DiisopropylethylamineHCID 96233N-Benzyl-2-chloroacetamide2×

Product 1

HCID 22257872HCID 22257872, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of N-benzyl-2-chloroacetamide (8.3 g—obtained as described for intermediate 1), DIPEA (9.31 mL) and 4-fluoro-aniline (4.28 mL) in anhydrous DMF (60 mL) was stirred at 100° C. for 24 hours under a Nitrogen atmosphere and then left at r.t. for two days. The solution was poured into water (100 mL) and extracted with AcOEt (2×200 mL). The combined organic extracts were washed with brine (100 mL), dried and concentrated in vacuo. The residue was purified by flash chromatography (CH/AcOEt 7:3) to give the title compound (7.73 g) as a beige solid.

Workup

  1. waitleft at r.t. for two days
  2. extractionextracted with AcOEt (2×200 mL)
  3. washThe combined organic extracts were washed with brine (100 mL)
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (CH/AcOEt 7:3)

Sources & evidence

ORD record
ord-7cee7df30e6d4a8a83fab13a530c455a
Source dataset
uspto-grants-2007_05
Patent number
US07214680B2

Reaction notes

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