Triethylamine → HCID 71617107, compound

HRID 930879Notes

Reaction equation

HRID 930879 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH:20]2[CH2:24][CH2:23][O:22][CH2:21]2)=[C:6]([C:8]2[C:9]3[CH:18]=[CH:17][NH:16][C:10]=3[C:11](=[O:15])[N:12]([CH3:14])[CH:13]=2)[CH:7]=1.C(N(CC)CC)C.[F:32][CH2:33][CH2:34][S:35](Cl)(=[O:37])=[O:36].[Cl-].[NH4+]>ClCCl>[F:32][CH2:33][CH2:34][S:35]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH:20]2[CH2:24][CH2:23][O:22][CH2:21]2)=[C:6]([C:8]2[C:9]3[CH:18]=[CH:17][NH:16][C:10]=3[C:11](=[O:15])[N:12]([CH3:14])[CH:13]=2)[CH:7]=1)(=[O:37])=[O:36]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 69806Ethanesulfonyl chloride, 2-fluoro-HCID 86721035HCID 86721035, compound

Product 1

HCID 71617107HCID 71617107, compoundYield 6.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of Example 91b (80.0 mg, 0.246 mmol) and triethylamine (74.6 mg, 0.738 mmol) in dichloromethane (4 mL) was added dropwise 2-fluoroethanesulfonyl chloride (144 mg, 0.984 mmol), and the reaction mixture was stirred at about ambient temperature for about 1 hour. The reaction mixture was neutralized with saturated aqueous ammonium chloride solution (50 mL) and the mixture was extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution, dried (anhydrous magnesium sulfate), filtered, and concentrated. The residue was purified by preparative HPLC (C18, 10-80% acetonitrile in 0.1% TFA/water) to provide the title compound (7.0 mg, 6.5% yield). 1H NMR (300 MHz, CDCl3) ppm 11.54 (bs, 1H), 7.45 (t, J=2.8 Hz, 1H), 7.19 (s, 1H), 6.88 (d, J=8.7 Hz, 1H), 6.73 (d, J=2.7 Hz, 1H) 6.67 (dd, J=3.1, 8.8 Hz, 1H), 6.40 (dd, J=2.0, 2.7 Hz, 1H), 4.76 (m, 1H), 3.82 (s, 3H), 3.85-3.62 (m, 8H), 2.97 (bs, 1H), 2.24-1.85 (m, 2H). MS (ESI+) m/z 436.2 (M+H)+.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×50 mL)
  2. washThe combined organic layers were washed with saturated aqueous sodium chloride solution
  3. dry with materialdried (anhydrous magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by preparative HPLC (C18, 10-80% acetonitrile in 0.1% TFA/water)

Sources & evidence

ORD record
ord-cbd6be82466643f796689e208c1bd906
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

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