HCID 117677454, compound → HCID 117677809, compound

HRID 1507485Notes

Reaction equation

HRID 1507485 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11]([NH:22][C@H:23]2[C@@H:27]3[O:28][C:29]([CH3:32])([CH3:31])[O:30][C@@H:26]3[C@@H:25]([CH2:33][OH:34])[CH2:24]2)=[N:12][C:13](S(C)(=O)=O)=[N:14][C:15]=1[O:16][CH3:17].[CH3:35][CH2:36][Mg+].[Br-]>C1COCC1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11]([NH:22][C@H:23]2[C@@H:27]3[O:28][C:29]([CH3:31])([CH3:32])[O:30][C@@H:26]3[C@@H:25]([CH2:33][OH:34])[CH2:24]2)=[N:12][C:13]([CH2:35][CH3:36])=[N:14][C:15]=1[O:16][CH3:17]

Participants

4

Reactant 2

HCID 117677454HCID 117677454, compoundHCID 178461630HCID 178461630, compound

Product 1

HCID 117677809HCID 117677809, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Compound 8 (100 mg, 0.197 mmol) was dissolved in THF (2 ml) and cooled to 0° C. EtMgBr (0.592 ml, 0.592 mmol, 1.0 M in THF) was added dropwise and stirred at 0° C. The reaction was quenched at 0° C. with sat. NH4Cl, diluted with water and EtOAc. The aqueous layer was extracted with EtOAc three times, dried (MgSO4), filtered and evaporated to dryness. The residue was purified by column chromatography on silica gel, eluting with CH2C2/MeOH to give the title compound as a colorless solid. 1H NMR (CDCl3) δ 10.58 (d, J=6.0 Hz, 1H), 7.96 (d, J=7.6 Hz, 1H), 7.88 (d, J=7.6 Hz, 1H), 7.46 (t, J=6.8 Hz, 1H), 7.33 (t, J=6.8 Hz, 1H), 4.75-4.69 (m, 2H), 4.63-4.61 (m, 1H), 4.16 (s, 3H), 3.84 (d, J=6.8 Hz, 1H), 2.76 (q, J=6.8, 1.2 Hz, 2H), 2.61-2.53 (m, 1H), 2.45-2.41 (m, 1H), 1.81-1.75 (m, 1H), 1.75 (s, 3H), 1.34 (s, 3H), 1.33 (t, J=6.8 Hz, 3H); LCMS 2.61 min, 457 (M+H)

Workup

  1. customThe reaction was quenched at 0° C. with sat. NH4Cl
  2. additiondiluted with water and EtOAc
  3. extractionThe aqueous layer was extracted with EtOAc three times
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was purified by column chromatography on silica gel
  8. washeluting with CH2C2/MeOH

Sources & evidence

ORD record
ord-39527c4a362a40968fd2ac61d95d4c55
Source dataset
uspto-grants-2015_12
Patent number
US09221809B2

Reaction notes

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