Triethylamine → HCID 71293413, compound

HRID 570866Notes

Reaction equation

HRID 570866 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]([C:24]2[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=2)[N:7]=[C:8]([NH:22][NH2:23])[N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[C:10]=1[CH3:11])=[O:4].C(N(CC)CC)C.Cl[C:40]([O:42][CH2:43]C)=[O:41]>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[CH:6]([C:24]2[CH:25]=[CH:26][C:27]([C:30]#[N:31])=[CH:28][CH:29]=2)[N:7]=[C:8]([NH:22][NH:23][C:40]([O:42][CH3:43])=[O:41])[N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:19])([F:20])[F:21])[CH:13]=2)[C:10]=1[CH3:11])=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 71293444HCID 71293444, compound

Product 1

HCID 71293413HCID 71293413, compoundYield 5.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Intermediate 2 (724 mg, 1.7 mmol) was dissolved in THF (20 mL) and cooled to 0° C. before addition of triethylamine (362 μL, 2.6 mmol) and ethyl chloroformate (191 μL, 2 mmol). The reaction mixture was stirred at 0° C. for 1 hour and then partitioned between EtOAc and water. The organic layer was separated, washed with brine, dried (Na2SO4) and evaporated in vacuo. The resultant residue was triturated with EtOAc, filtered and the solid collected to yield the title compound as a white solid (49 mg).

Workup

  1. custompartitioned between EtOAc and water
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo
  6. customThe resultant residue was triturated with EtOAc
  7. filtrationfiltered
  8. customthe solid collected

Sources & evidence

ORD record
ord-8b399295b592478dac13c39edfd199fe
Source dataset
uspto-grants-2015_05
Patent number
US09023855B2

Reaction notes

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