Water → HCID 22174526, compound

HRID 1797321Notes

Reaction equation

HRID 1797321 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH2:16][CH2:17][CH2:18]O)[CH:5]=[CH:4][C:3]=1[C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH3:28])=[O:21].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[NH:40]1[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1.O>N1C=CC=CC=1.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH2:16][CH2:17][CH2:18][N:40]2[CH2:45][CH2:44][O:43][CH2:42][CH2:41]2)[CH:5]=[CH:4][C:3]=1[C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH3:28])=[O:21]

Participants

7

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8083MorpholineHCID 22174543HCID 22174543, compound

Product 1

HCID 22174526HCID 22174526, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound 198 (100 mg, 0.25 mmol) was dissolved in dry pyridine (130 μL) under an argon atmosphere. The solution was cooled on an ice bath and 4-toluenesulfonyl chloride (48 mg, 0.25 mmol) was added. The reaction mixture was quenched with water after 45 min at room temperature. The aqueous phase was extracted twice with EtOAc. The combined organic phases were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography using petroleum ether/EtOAc 4:1 as the eluent. The tosylate was dissolved in dry DMF (2.0 mL) and morpholine (17 μL, 0.19 mmol) was added. The reaction mixture was stirred for 48 h at room temperature and then poured into a mixture of water and EtOAc. The aqueous phase was extracted with more EtOAc (×2). The combined organic phases were washed with water, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography using DCM/MeOH 100:4 as the eluent to afford the title compound as a yellow oil.

Workup

  1. temperatureThe solution was cooled on an ice bath
  2. customThe reaction mixture was quenched with water after 45 min at room temperature
  3. extractionThe aqueous phase was extracted twice with EtOAc
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography
  9. dissolutionThe tosylate was dissolved in dry DMF (2.0 mL)
  10. extractionThe aqueous phase was extracted with more EtOAc (×2)
  11. washThe combined organic phases were washed with water
  12. dry with materialdried (MgSO4)
  13. filtrationfiltered
  14. concentrationconcentrated in vacuo
  15. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-7aa66b57689b401ba0449bb7de3096ec
Source dataset
uspto-grants-2006_04
Patent number
US07034015B2

Reaction notes

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