Dichloromethane → HCID 66967035, compound

HRID 1711846Notes

Reaction equation

HRID 1711846 reaction equation
C([O:5][C:6](=[O:19])/[CH:7]=[CH:8]/[C:9]1[CH:10]=[C:11]2[O:17][C:16](=[O:18])[NH:15][C:12]2=[N:13][CH:14]=1)(C)(C)C.[Cl:20]CCl>FC(F)(F)C(O)=O>[ClH:20].[O:18]=[C:16]1[NH:15][C:12]2=[N:13][CH:14]=[C:9](/[CH:8]=[CH:7]/[C:6]([OH:19])=[O:5])[CH:10]=[C:11]2[O:17]1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 59456950HCID 59456950, compound

Product 1

HCID 66967035HCID 66967035, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (E)-3-(2-oxo-2,3-dihydro-oxazolo[4,5-b]pyridine-6-yl)acrylic acid tert-butyl ester (274 mg, 1.04 mmol) in dichloromethane (5 mL) and trifluoroacetic acid (5 mL) was stirred for 30 min, then the solvents were removed in vacuo. The residue was suspended in anhydrous HCl (5 mL of a 4 M solution in 1,4-dioxane, 20 mmol) and the mixture was sonicated for 1 min. The resulting solid was collected by filtration, washed with diethyl ether and then dried in vacuo to give the title compound (194 mg, 77%) as a light brown solid: 1H NMR (300 MHz, DMSO-d6) δ 8.31 (s, 1H), 8.13 (s, 1H), 7.63 (d, J=16.0 Hz, 1H), 6.60 (d, J=16.0 Hz, 1H).

Workup

  1. customthe solvents were removed in vacuo
  2. customwas sonicated for 1 min
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with diethyl ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-a6bfc56b4b044cd59e15acb3ca434660
Source dataset
uspto-grants-2010_09
Patent number
US07790709B2

Reaction notes

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