Benzyl Bromide → HCID 52950482, compound

HRID 1521864Notes

Reaction equation

HRID 1521864 reaction equation
[N:1]1([C:7]([C:9]2[C:10]3[CH2:27][S:26](=[O:29])(=[O:28])[C:25]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[C:11]=3[N:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:13]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[H-].[Na+].[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C1COCC1>[CH2:32]([CH:27]1[C:10]2[C:9]([C:7]([N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)=[O:8])=[N:13][N:12]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:11]=2[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=2[S:26]1(=[O:28])=[O:29])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 66578983HCID 66578983, compound

Product 1

HCID 52950482HCID 52950482, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(morpholin-4-ylcarbonyl)-1-phenyl-1,4-dihydrothiochromeno[4,3-c]pyrazole 5,5-dioxide (100 mg; 0.24 mmol; 1.0 eq.) in THF (4.0 mL) is added NaH (55% w/w in mineral oil) (12.79 mg; 0.29 mmol; 1.2 Eq.). After 15 min stirring, benzyl bromide (34.81 μL; 0.29 mmol; 1.2 eq.) is added and the reaction mixture is stirred at room temperature for 3h. The reaction is quenched with water and the product extracted with EtOAc. The combined organic phases are washed with brine, dried over MgSO4 and concentrated under reduced pressure. The crude residue is recrystallized from EtOH and dried under vacuum to afford the title compound as an off-white solid. 1H NMR (DMSO-d6, 300MHz) δ 8.01-7.98 (m, 1H), 7.63-7.58 (m, 4H), 7.53-7.46 (m, 3H), 7.12-7.07 (m, 3H), 6.89-6.86 (m, 2H), 6.66-6.64 (m, 1H), 5.29-5.25 (m, 1H), 3.93-3.88 (m, 1H), 3.63-3.53 (m, 5H), 3.45-3.36 (m, 2H), 3.26-3.20 (m, 1H), 2.76-2.69 (m, 1H). UPLC/MS: (ES+): 500.2, (ES−): 498.3. HPLC (max plot) 97.6%; Rt 4.32 min.

Workup

  1. stirringthe reaction mixture is stirred at room temperature for 3h
  2. customThe reaction is quenched with water
  3. extractionthe product extracted with EtOAc
  4. washThe combined organic phases are washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue is recrystallized from EtOH
  8. customdried under vacuum

Sources & evidence

ORD record
ord-467d5449ea1442b795f0e450702f1c62
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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