Triethylamine → HCID 10072592, compound

HRID 1676998Notes

Reaction equation

HRID 1676998 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][S:5]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Br:17])[CH:15]=2)[NH:10][C:9]=1[C:18]([NH2:20])=[O:19])(=[O:7])=[O:6].C(N(CC)CC)C.[CH2:28]([S:30](Cl)(=[O:32])=[O:31])[CH3:29]>CCOC(C)=O>[Br:17][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([C:18]([NH2:20])=[O:19])=[C:8]2[S:5]([NH:4][CH2:3][CH2:2][NH:1][S:30]([CH2:28][CH3:29])(=[O:32])=[O:31])(=[O:6])=[O:7]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 11667Ethanesulfonyl chloride2×HCID 10248012HCID 10248012, compound

Product 1

HCID 10072592HCID 10072592, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

A solution of the product from Example 63 (15 mg, 0.038 mmol), triethylamine (0.017 mL, 0.11 mmol) and ethanesulfonyl chloride (0.004 mL, 0.04 mmols) were combined in a sealed tube and heated to 65° C. overnight. The solvent was removed under a stream of N2 and replaced with DMF. After adding an additional 3 equivalents of ethanesulfonyl chloride and triethylamine, the reaction was heated to 65° C. for 8 hours and stirred at room temperature for 60 hours. The mixture was diluted with EtOAc and washed with 10% Na2CO3 and brine, dried over Na2SO4, filtered and concentrated in vac o. Purification by reversed-phase preparative HPLC gave the titled compound. ESI+ MS: 453 [M+H]+.

Workup

  1. customThe solvent was removed under a stream of N2
  2. temperaturethe reaction was heated to 65° C. for 8 hours
  3. washwashed with 10% Na2CO3 and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vac o
  7. customPurification by reversed-phase preparative HPLC

Sources & evidence

ORD record
ord-9dddbb15f8e9441785da46e3de7943e5
Source dataset
uspto-grants-2011_08
Patent number
US08008295B2

Reaction notes

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