HCID 68093065, compound → HCID 66685692, compound

HRID 1778373Notes

Reaction equation

HRID 1778373 reaction equation
[CH2:1]([N:3]([CH2:36][CH3:37])[CH2:4]/[CH:5]=[CH:6]\[C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[S:14]([NH:17][C:18]1[CH:31]=[CH:30][C:21]2[C:22]3[CH:23]=[CH:24][O:25][C:26]=3[CH2:27][CH2:28][O:29][C:20]=2[C:19]=1[C:32]([O:34][CH3:35])=[O:33])(=[O:16])=[O:15])[CH3:2]>C(O)C.C(O)=O>[CH2:36]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[S:14]([NH:17][C:18]1[CH:31]=[CH:30][C:21]2[C:22]3[CH:23]=[CH:24][O:25][C:26]=3[CH2:27][CH2:28][O:29][C:20]=2[C:19]=1[C:32]([O:34][CH3:35])=[O:33])(=[O:16])=[O:15])[CH3:37]

Participants

4

Reactant 1

HCID 68093065HCID 68093065, compound2×

Product 1

HCID 66685692HCID 66685692, compoundYield 90.8%

Reagents, catalysts & solvents 2

HCID 284Formic AcidCatalystHCID 702EthanolSolvent

Procedure

Methyl 8-[2((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-4,5-dihydro-3,6-dioxabenzo[e]azulene-7-carboxylate (Intermediate 5, 0.147 g) was suspended in ethanol. Formic acid (2 drops) was added and the flask was evacuated and purged with nitrogen gas. Palladium hydroxide (20% wt, 0.015 g) was added and nitrogen was replaced by hydrogen and the mixture was stirred at room temperature under an atmosphere of hydrogen for 1 hour. The mixture was filtered through a pad of Celite and washed with ethanol. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of methanol and DCM, with a gradient of 2.5-10% to give methyl 8-[2-(3-diethylaminopropyl)-4-fluorobenzenesulfonylamino]-4,5-dihydro-3,6-dioxabenzo[e]azulene-7-carboxylate (0.134 g) as a yellow glassy solid.

Workup

  1. customthe flask was evacuated
  2. custompurged with nitrogen gas
  3. additionPalladium hydroxide (20% wt, 0.015 g) was added
  4. filtrationThe mixture was filtered through a pad of Celite
  5. washwashed with ethanol
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was purified by chromatography on silica
  8. washeluting with a mixture of methanol and DCM, with a gradient of 2.5-10%

Sources & evidence

ORD record
ord-abfbbc610d5343058a9132edb5600ce1
Source dataset
uspto-grants-2016_02
Patent number
US09266896B2

Reaction notes

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