Benzoyl chloride → HCID 46186187, compound

HRID 341286Notes

Reaction equation

HRID 341286 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([CH2:19][CH2:20][NH2:21])=[CH:16][CH:17]=3)[C:12]3[CH:22]=[C:23]([Cl:26])[CH:24]=[N:25][C:11]2=3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(CC)CC.[C:34](Cl)(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(Cl)Cl>[Cl:26][C:23]1[CH:24]=[N:25][C:11]2[N:10]([S:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)(=[O:9])=[O:8])[C:18]3[C:13]([C:12]=2[CH:22]=1)=[CH:14][C:15]([CH2:19][CH2:20][NH:21][C:34](=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[CH:16][CH:17]=3

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 46186186HCID 46186186, compound

Product 1

HCID 46186187HCID 46186187, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled mixture (0° C.) of 16 (65 mg, 0.17 mmol) in CH2Cl2 (3 mL) were added Et3N (100 μL, 4.2 equiv.) and benzoyl chloride (30 μL, 1.5 equiv.). The mixture was stirred for 12 h at room temperature. The resulting mixture was then quenched at 0° C. with NaHCO3. It was extracted with the mixture of EtOAc. The resulting organic layer was washed with saturated aqueous NaHCO3 solution and brine, dried over MgSO4, filtered and solvents were removed under reduced pressure. The crude product was purified by flash chromatography (EtOAc/PE 1:1) to afford 17 in 48% yield as a white solid, 1H NMR (300 MHz, CDCl3): δ 8.48 (d, 1H, J=2.3 Hz), 8.41 (d, 1H, J=8.5 Hz), 8.13-8.11 (m, 3H), 7.77 (bs, 1H), 7.70 (d, 1H, J=7.5 Hz), 7.57-7.41 (m, 7H), 6.19 (bs, 1H), 3.05 (q, 2H, J=6.9 Hz), 3.09 (t, 2H, J=6.9 Hz); MS (ESI) m/z 490 [M+H+]

Workup

  1. customThe resulting mixture was then quenched at 0° C. with NaHCO3
  2. extractionIt was extracted with the mixture of EtOAc
  3. washThe resulting organic layer was washed with saturated aqueous NaHCO3 solution and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customsolvents were removed under reduced pressure
  7. customThe crude product was purified by flash chromatography (EtOAc/PE 1:1)

Sources & evidence

ORD record
ord-5cd999a84fc1460ebfca3689ca51bd59
Source dataset
uspto-grants-2014_11
Patent number
US08895744B2

Reaction notes

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