HCID 86657755, compound → HCID 46847412, compound

HRID 383778Notes

Reaction equation

HRID 383778 reaction equation
[Cu][C:2]#[N:3].I[C:5]1[CH:10]=[C:9]([C:11]([N:13]2[CH2:17][CH2:16][CH:15]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[CH2:14]2)=[O:12])[CH:8]=[CH:7][C:6]=1[C:24]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[C:26]([C:34]([F:37])([F:36])[F:35])[CH:25]=1>CS(C)=O>[N:20]1[CH:21]=[CH:22][CH:23]=[C:18]([CH:15]2[CH2:16][CH2:17][N:13]([C:11]([C:9]3[CH:10]=[C:5]([C:2]#[N:3])[C:6]([C:24]4[CH:25]=[C:26]([C:34]([F:35])([F:36])[F:37])[CH:27]=[C:28]([C:30]([F:33])([F:31])[F:32])[CH:29]=4)=[CH:7][CH:8]=3)=[O:12])[CH2:14]2)[CH:19]=1

Participants

4

Reactant 2

HCID 86657755HCID 86657755, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 46847412HCID 46847412, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
180 °C

Procedure

Copper(I) cyanide (42.9 mg, 0.479 mmol) was added to a stirred solution of 4b (200 mg, 0.368 mmol) in DMSO (4.00 mL), and the resulting mixture was heated to 180° C. for 12 h. The reaction mixture was cooled to rt, quenched with satd. aq. NH4Cl and extracted with EtOAc. The combined organics were washed with water and brine, dried (sodium sulfate) and concentrated in vacuo. The resulting crude residue was purified by preparative reversed phase HPLC on YMC Pack Pro C18 stationary phase (CH3CN/H2O as eluent, 0.05% TFA as modifier), followed by lyophilization of the purified fractions to afford the title compound 6a. m/z (ES) 490 (MH)+.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. customquenched with satd
  3. extractionaq. NH4Cl and extracted with EtOAc
  4. washThe combined organics were washed with water and brine
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated in vacuo
  7. customThe resulting crude residue was purified by preparative reversed phase HPLC on YMC Pack Pro C18 stationary phase (CH3CN/H2O as eluent, 0.05% TFA as modifier)

Sources & evidence

ORD record
ord-8a8968a3ce3841c3a1195af85d28781f
Source dataset
uspto-grants-2013_02
Patent number
US08367679B2

Reaction notes

Loading…