Methanol → HCID 69435327, compound

HRID 404907Notes

Reaction equation

HRID 404907 reaction equation
[OH:1][N:2]=[C:3]([C:5]1[S:9][C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH:18]([CH3:20])[CH3:19])=[CH:13][CH:12]=2)=[N:7][CH:6]=1)[NH2:4].[O:21]=[C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24](=[O:31])[N:23]1[CH:32]([CH3:36])[C:33](Cl)=O.CO>N1C=CC=CC=1>[CH:18]([O:17][C:14]1[CH:15]=[CH:16][C:11]([O:10][C:8]2[S:9][C:5]([C:3]3[N:4]=[C:36]([CH:32]([N:23]4[C:24](=[O:31])[C:25]5[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=5)[C:22]4=[O:21])[CH3:33])[O:1][N:2]=3)=[CH:6][N:7]=2)=[CH:12][CH:13]=1)([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 887MethanolHCID 4914672HCID 4914672, compoundHCID 90774845HCID 90774845, compound

Product 1

HCID 69435327HCID 69435327, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of Example 40B (616 mg, 2.1 mmol) in pyridine (15 mL) was added 2-(1,3-dioxoisoindolin-2-yl)propanoyl chloride (CAS#5364-22-7) (598 mg, 2.52 mmol) and the solution was stirred for an hour at room temperature and then at reflux for an additional hour. The reaction mixture was cooled down, methanol was added, and after stirring for 15 minutes the solvent was removed under vacuum. The title compound was purified via silica-gel column chromatography using a gradient of 25 to 50% ethyl acetate in hexane to provide 855 mg, 1H NMR (300 MHz, CDCl3) δ ppm 7.84-7.96 (m, 3H) 7.73-7.83 (m, 2H) 7.15-7.24 (m, 2H) 6.86-6.99 (m, 2H) 5.68 (q, J=7.35 Hz, 1H) 4.43-4.63 (m, 1H) 1.98 (d, J=7.35 Hz, 3H) 1.35 (d, J=5.88 Hz, 6H). MS (DCI): m/z 477 (M+H)+.

Workup

  1. temperatureat reflux for an additional hour
  2. temperatureThe reaction mixture was cooled down
  3. stirringafter stirring for 15 minutes the solvent
  4. customwas removed under vacuum
  5. customThe title compound was purified via silica-gel column chromatography
  6. customto provide 855 mg, 1H NMR (300 MHz, CDCl3) δ ppm 7.84-7.96 (m, 3H) 7.73-7.83 (m, 2H) 7.15-7.24 (m, 2H) 6.86-6.99 (m, 2H) 5.68 (q, J=7.35 Hz, 1H) 4.43-4.63 (m, 1H) 1.98 (d, J=7.35 Hz, 3H) 1.35 (d, J=5.88 Hz, 6H)

Sources & evidence

ORD record
ord-8ac9c5d413d64f97bf2266b08d285da3
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

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