HCID 68157224, compound → HCID 68157429, compound

HRID 242907Notes

Reaction equation

HRID 242907 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][C@H:8]([C:10](=O)[NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]#[N:26])[CH:20]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2]>CC(O)=O>[C:1]([O:5][C:6](=[O:28])[NH:7][C@H:8]([C:10]1[N:18]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]#[N:26])[CH:20]=2)[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 68157224HCID 68157224, compound

Product 1

HCID 68157429HCID 68157429, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of {(S)-1-[2-(3-cyanophenylamino)phenylcarbamoyl]ethyl}carbamic acid tert-butyl ester (289 mg, 0.75 mmol) in AcOH (3 mL) was heated at 80° C. for 16 h. After cooling to RT, the volatiles were removed in vacuo and the residue dissolved in DCM and washed with a saturated aqueous solution of NaHCO3. The aqueous phase was further extracted with DCM (×3) and the combined organic fractions were dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-2% 2M NH3/MeOH in DCM) to afford the title compound (232 mg, 86%). The material was still impure and taken forward in the next step without further purification. LCMS (Method C): RT 3.54 min [M+H]+ 363.4

Workup

  1. customthe volatiles were removed in vacuo
  2. dissolutionthe residue dissolved in DCM
  3. washwashed with a saturated aqueous solution of NaHCO3
  4. extractionThe aqueous phase was further extracted with DCM (×3)
  5. dry with materialthe combined organic fractions were dried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-2% 2M NH3/MeOH in DCM)

Sources & evidence

ORD record
ord-d51cfdd7d54046289365f504f06c1485
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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