Pyridine → HCID 117949651, compound

HRID 1474430Notes

Reaction equation

HRID 1474430 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[C:4]([CH3:10])[C:3]=1[N:11]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].N1C=CC=CC=1.Cl[C:33]([O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])=[O:34]>O>[C:22]([O:21][C:19]([N:11]([C:3]1[C:4]([CH3:10])=[CH:5][C:6]([C:8]#[N:9])=[CH:7][C:2]=1[NH:1][C:33]([O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])=[O:34])[C:12](=[O:13])[O:14][C:15]([CH3:18])([CH3:16])[CH3:17])=[O:20])([CH3:25])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 1049PyridineHCID 118547Carbonochloridic acid, heptyl esterHCID 131732766HCID 131732766, compound

Product 1

HCID 117949651HCID 117949651, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Di-t-butyl (2-amino-4-cyano-6-methylphenyl)imidodicarbonate (104 mg, 0.3 mmol) obtained in Step 2 was added with pyridine (0.24 mL, 3 mmol, 10 eq) and heptyl chloroformate (0.11 mL, 0.6 mmol, 2 eq), and the mixture thus obtained was stirred at room temperature for 10 minutes, followed by further stirring at 80° C. for 2 hours. Upon completion of the reaction, the resulting product was added with distilled water, and extracted with ethyl acetate. The organic layer thus obtained was dried over MgSO4, and concentrated under reduced pressure. Subsequently, the residue was purified by silica gel column chromatography (EA:Hex=1:9) to obtain the title compound in a colorless liquid (146 mg, yield: 99%).

Workup

  1. customthe mixture thus obtained
  2. stirringby further stirring at 80° C. for 2 hours
  3. customUpon completion of the reaction
  4. extractionextracted with ethyl acetate
  5. customThe organic layer thus obtained
  6. dry with materialwas dried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customSubsequently, the residue was purified by silica gel column chromatography (EA:Hex=1:9)

Sources & evidence

ORD record
ord-0219344a885146c3b45917cbfdd903af
Source dataset
uspto-grants-2015_04
Patent number
US09018233B2

Reaction notes

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