2-Fluoropyrazine → HCID 67185883, compound

HRID 885989Notes

Reaction equation

HRID 885989 reaction equation
[CH3:1][C:2]1([CH3:23])[NH:7][C:6](=[O:8])[C:5]2[S:9][C:10]([N:12]3[C:17]4[CH:18]=[C:19]([OH:22])[CH:20]=[CH:21][C:16]=4[O:15][CH2:14][CH2:13]3)=[N:11][C:4]=2[CH2:3]1.F[C:25]1[CH:30]=[N:29][CH:28]=[CH:27][N:26]=1.CC(C)([O-])C.[Na+]>C1COCC1>[CH3:1][C:2]1([CH3:23])[NH:7][C:6](=[O:8])[C:5]2[S:9][C:10]([N:12]3[C:17]4[CH:18]=[C:19]([O:22][C:25]5[CH:30]=[N:29][CH:28]=[CH:27][N:26]=5)[CH:20]=[CH:21][C:16]=4[O:15][CH2:14][CH2:13]3)=[N:11][C:4]=2[CH2:3]1

Participants

5

Reactant 3

HCID 6428352-FluoropyrazineHCID 23676156Sodium t-butoxideHCID 671855836,6-Dimethyl-2-(6-hydroxy-2,3-dihydrobenzo[1,4]oxazin-4-yl)-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4(5h)-one

Product 1

HCID 67185883HCID 67185883, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of Example 57 (70 mg, 0.211 mmol) in THF (4 mL) was added 2-fluoropyrazine (41 mg, 0.423 mmol) and sodium tert-butoxide (81 mg, 0.846 mmol). The reaction was heated to 150° C. under microwave irradiation for 50 minutes then cooled to r.t. The resulting precipitate was collected, washed with water (4×10 mL), Et2O (3×10 mL) and dried in vacuo to yield the title compound (35 mg, 41%) as an off-white solid. δH (CDCl3) 8.44 (1H, d, J 1.3 Hz), 8.26 (1H, d, J 2.6 Hz), 8.12 (1H, dd, J 2.8 and 1.5 Hz), 8.02 (1H, d, J 2.6 Hz), 7.01 (1H, d, J 8.9 Hz), 6.86 (1H, dd, J 8.9 and 2.6 Hz), 5.26 (1H, s), 4.42-4.30 (2H, m), 4.15-4.10 (2H, m), 2.86 (2H, s), 1.38 (6H, s). LCMS (ES+) 410.0 (M+H)+, RT 3.04 minutes (Method 2).

Workup

  1. temperaturethen cooled to r.t
  2. customThe resulting precipitate was collected
  3. washwashed with water (4×10 mL), Et2O (3×10 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-9999674f21f346eca5f4a7a51f3c073a
Source dataset
uspto-grants-2012_08
Patent number
US08242116B2

Reaction notes

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