Dichloromethane → HCID 66967035, compound

HRID 1362095Notes

Reaction equation

HRID 1362095 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-8b1748c8ef9c4dcba9e7d32cf413dcaf
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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