Acetyl chloride → (2-Bromo-4-fluoro-6-{6-oxo-8-thia-4,5-diazatricyclo[7.4.0.02,7]trideca-1 (9),2 (7),3-trien-5-yl}phenyl)methyl acetate

HRID 1774647Notes

Reaction equation

HRID 1774647 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Br:8])[C:5]([CH2:9][OH:10])=[C:4]([N:11]2[C:23](=[O:24])[C:22]3[S:21][C:20]4[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=4[C:14]=3[CH:13]=[N:12]2)[CH:3]=1.CCN(CC)CC.[C:32](Cl)([CH3:34])=[O:33]>C1COCC1.O>[C:15]12[CH2:16][CH2:17][CH2:18][CH2:19][C:20]=1[S:21][C:22]1[C:23](=[O:24])[NH:11][N:12]=[CH:13][C:14]2=1.[C:32]([O:10][CH2:9][C:5]1[C:6]([Br:8])=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[N:11]1[C:23](=[O:24])[C:22]2[S:21][C:20]3[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=3[C:14]=2[CH:13]=[N:12]1)(=[O:33])[CH3:34]

Participants

7

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 118116415(4-Fluoro-2-{6-oxo-8-thia-4,5-diazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3-triene-5-yl}-6-(bromo)phenyl)carbinol2×

Product 2

HCID 58044224(2-Bromo-4-fluoro-6-{6-oxo-8-thia-4,5-diazatricyclo[7.4.0.02,7]trideca-1 (9),2 (7),3-trien-5-yl}phenyl)methyl acetateHCID 670165536,7,8,9-Tetrahydrobenzo[4,5]thieno[2,3-d]pyridazin-4(3H)-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

8-thia-4,5-diazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3-trien-6-one was prepared following the procedures of U.S. Pat. No. 8,716,274, Example 191d and converted to (4-fluoro-2-{6-oxo-8-thia-4,5-diazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3-triene-5-yl}-6-(bromo)phenyl)carbinol 108a. To a mixture of 108a (4.1 g, 10 mmol) and Et3N (1.95 mL, 14 mmol) in THF (50 mL) was added AcCl (0.85 mL, 12 mmol). The mixture was stirred at rt for 1 h, diluted with water and extracted with EA. The combined organic layers were dried over Na2SO4, filtered and concentrated to give compound 108b (4.0 g) as yellow solid. MS-ESI: [M+H]+ 451.0

Workup

  1. extractionextracted with EA
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8a665bad32ad42eda8a5e21260cb1e6f
Source dataset
uspto-grants-2016_02
Patent number
US09260415B2

Reaction notes

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