Water → HCID 86591623, compound

HRID 1295721Notes

Reaction equation

HRID 1295721 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15](=[O:20])[NH:16][CH:17]=[CH:18][N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC([O-])(C)C.[K+].[F:27][C:28]1[CH:42]=[C:41]([F:43])[C:40]([F:44])=[CH:39][C:29]=1[O:30][CH2:31][CH2:32][CH2:33]OS(C)(=O)=O.O>C1COCC1>[F:27][C:28]1[CH:42]=[C:41]([F:43])[C:40]([F:44])=[CH:39][C:29]=1[O:30][CH2:31][CH2:32][CH2:33][N:16]1[CH:17]=[CH:18][N:19]=[C:14]([N:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:13][CH2:12]2)[C:15]1=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 590138923-(4-tert-Butoxycarbonyl-1-piperazinyl)-2(1H)-pyrazinoneHCID 86591624HCID 86591624, compound

Product 1

HCID 86591623HCID 86591623, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 3-(4-tert-butoxycarbonyl-1-piperazinyl)-2(1H)-pyrazinone (0.83 g, 3.0 mmol; from Example 48, Step 1) and t-BuOK (497 mg, 4.4 mmol) in THF (5 mL) was stirred for 10 min, and then added to methanesulfonic acid 3-(2,4,5-trifluoro-phenoxy)-propyl ester (0.80 g, 3.0 mmol; from Step 2) in THF (50 mL). After being stirred at room temperature for 1 day, HPLC showed about 20% conversion. After 6 days, the reaction was worked up: water was added, THF was evaporated and the aqueous mixture was extracted twice with EtOAc, dried and concentrated to yield 1.33 g of the crude product as a yellow oil. HPLC analysis showed a 1/1 ratio between the title product and the isomeric O-alkylated product. Purification by chromatography on silica gel using EtOAc/hexane (1/3 to 1/1.7) as eluent gave 427 mg (30%) of the title product as a colorless oil. HPLC purity: 96%. MS m/z 469 (M+H)+.

Workup

  1. stirringAfter being stirred at room temperature for 1 day
  2. waitAfter 6 days
  3. customTHF was evaporated
  4. extractionthe aqueous mixture was extracted twice with EtOAc
  5. customdried
  6. concentrationconcentrated
  7. customto yield 1.33 g of the crude product as a yellow oil

Sources & evidence

ORD record
ord-aff406b0967f4e9b8b2b6616e8c5eb7d
Source dataset
uspto-grants-2007_07
Patent number
US07244722B2

Reaction notes

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