Trichloroacetonitrile → HCID 67348767, compound

HRID 1672762Notes

Reaction equation

HRID 1672762 reaction equation
[C:1]([NH:4][NH:5][C:6](=O)[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N:13]2[CH2:22][CH:21]3[N:17]([CH2:18][CH2:19][CH2:20]3)[C:16]3[N:23]=[C:24]([NH:27][CH2:28][CH3:29])[N:25]=[CH:26][C:15]=3[C:14]2=[O:30])[CH:8]=1)(=[O:3])[CH3:2].ClC(Cl)(Cl)C#N.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C>[CH2:28]([NH:27][C:24]1[N:25]=[CH:26][C:15]2[C:14](=[O:30])[N:13]([C:9]3[CH:10]=[CH:11][CH:12]=[C:7]([C:6]4[O:3][C:1]([CH3:2])=[N:4][N:5]=4)[CH:8]=3)[CH2:22][CH:21]3[N:17]([CH2:18][CH2:19][CH2:20]3)[C:16]=2[N:23]=1)[CH3:29]

Participants

5

Reactant 3

HCID 11011TrichloroacetonitrileHCID 11776Triphenylphosphine2×HCID 67351816HCID 67351816, compound

Product 1

HCID 67348767HCID 67348767, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

Compound 19 (136 mg, 0.320 mmol) obtained in Example 19 was dissolved in acetonitrile (2.1 mL), and the mixture was stirred for 1 hour under microwave (CEM; Discover, 300 watts, 150° C.) irradiation after adding trichloroacetonitrile (0.0646 mL, 0.640 mmol) and triphenylphosphine-supported resin (Triphenylphosphine, polymer-supported; 3.08 mmol P/G, 320 mg, 0.960 mmol). The resin was separated by filtration, and the filtrate was collected, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give the title compound (Compound 20) (108 mg, 83%).

Workup

  1. customThe resin was separated by filtration
  2. customthe filtrate was collected
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a819a3962c4f4c13bfca867519c72e42
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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