Acetic Acid → HCID 58109530, compound

HRID 2037446Notes

Reaction equation

HRID 2037446 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([CH2:28][CH2:29][OH:30])[O:13][C:12](=[O:14])[N:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[N:16]=2)[CH2:10][CH2:9]1.CC([O-])=O.[Na+].CC(O)=O.[Cl:40]N1C(=O)N(Cl)C(=O)N(Cl)C1=O>CC#N.O.C(Cl)Cl>[Cl:40][C:18]1[CH:19]=[CH:20][C:15]([N:11]2[CH2:10][CH2:9][C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])([CH2:28][CH2:29][OH:30])[O:13][C:12]2=[O:14])=[N:16][C:17]=1[C:21]1[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 6909Trichloroisocyanuric AcidHCID 517045Sodium AcetateHCID 58109406HCID 58109406, compound

Product 1

HCID 58109530HCID 58109530, compoundYield 48.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-(2-fluorophenyl)-3-(6-(4-fluorophenyl)pyridin-2-yl)-6-(2-hydroxyethyl)-1,3-oxazinan-2-one (30 mg, 0.07 mmol), NaOAc (9 mg, 0.11 mmol) in HOAc (4 mg, 0.07 mmol), CH3CN (2 mL), H2O (0.1 mL) and CH2Cl2 (2 mL) was stirred at rt for 5 min. A solution of 1,3,5-trichloro-1,3,5-triazinane-2,4,6-trione (37 mg, 0.11 mmol) in CH3CN (0.5 mL) was added slowly. The mixture was stirred for 20 min and heated to 40° C. for 2 h. The reaction was quenched with aq NaHSO3 and extracted with CH2Cl2. The organic layer was dried with Na2SO4, concentrated to afford the crude product. Purification afforded 3-(5-chloro-6-(4-fluorophenyl)pyridin-2-yl)-6-(2-fluorophenyl)-6-(2-hydroxyethyl)-1,3-oxazinan-2-one (15 mg, 48%). LC-MS Method 3, tR=1.331 min, m/z=445. 1H NMR (CDCl3, 400 Hz): 2.40 (m, 3H), 2.84 (m, 1H), 3.40 (m, 1H), 3.66 (m, 1H), 3.82 (m, 1H), 4.26 (m, 1H), 7.10 (m, 3H), 7.18 (m, 1H), 7.34 (m, 1H), 7.50 (m, 1H), 7.68 (m, 2H), 7.76 (m, 1H), 8.01 (m, 1H).

Workup

  1. stirringThe mixture was stirred for 20 min
  2. temperatureheated to 40° C. for 2 h
  3. customThe reaction was quenched with aq NaHSO3
  4. extractionextracted with CH2Cl2
  5. dry with materialThe organic layer was dried with Na2SO4
  6. concentrationconcentrated
  7. customto afford the crude product
  8. customPurification

Sources & evidence

ORD record
ord-d9d9548b5ec3427082ba1c27a2f23479
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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