Ethanolamine → HCID 58677582, compound

HRID 1012636Notes

Reaction equation

HRID 1012636 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=2[F:29])[CH:18]=[CH:17][C:3]=1[C:4]([C:6]1[CH:7]=[C:8]([S:13](Cl)(=[O:15])=[O:14])[CH:9]=[CH:10][C:11]=1[CH3:12])=[O:5].[CH2:30]([CH2:32][NH2:33])[OH:31]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:20]=[C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=2[F:29])[CH:18]=[CH:17][C:3]=1[C:4]([C:6]1[CH:7]=[C:8]([S:13]([NH:33][CH2:32][CH2:30][OH:31])(=[O:15])=[O:14])[CH:9]=[CH:10][C:11]=1[CH3:12])=[O:5]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 86606855HCID 86606855, compound

Product 1

HCID 58677582HCID 58677582, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound 496 (0.07 g, 0.15 mmol) was dissolved in pyridine (0.4 mL) and ethanolamine (0.011 mL, 0.18 mmol) was added. The solution was kept at room temperature for 1 h after which it was concentrated in vacuo. The residue was dissolved in EtOAc and H2O and the phases were separated. The water phase was extracted with EtOAc (×2) and the combined organic phases were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography using a gradient of EtOAc/petroleum ether (40-60) 3:7→1:0 as the eluent. This afforded the title compound as a solid. 13C NMR (CD3OD) δ 196.5, 161.2 (dd), 158.0 (dd), 151.9, 143.3, 142.0, 139.5, 136.5, 135.2, 133.2, 129.9, 128.2, 127.8, 127.8 (dd), 125.7 (dd), 116.5, 113.1, 112.7 (dd), 105.8 (dd), 61.8, 46.3, 20.3

Workup

  1. concentrationafter which it was concentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc
  3. customH2O and the phases were separated
  4. extractionThe water phase was extracted with EtOAc (×2)
  5. washthe combined organic phases were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-a823a5eeb4b5452eb470a51bcdd95f53
Source dataset
uspto-grants-2011_07
Patent number
US07977387B2

Reaction notes

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