Ammonium Chloride → 1-allyl-N-(4-fluoro-5-((4-bromo-2-chlorophenyl)amino)benzo[d]oxazol-6-yl)cyclopropane-1-sulfonamide

HRID 928986Notes

Reaction equation

HRID 928986 reaction equation
[CH2:1]([C:4]1([S:7]([N:10]2[C:14]3=[CH:15][C:16]4[O:20][CH:19]=[N:18][C:17]=4[C:21]([F:22])=[C:13]3[N:12]([C:23]3[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][C:24]=3[Cl:30])C2=O)(=[O:9])=[O:8])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].C[Si](C)(C)[O-].[K+].[NH4+].[Cl-]>C1COCC1>[CH2:1]([C:4]1([S:7]([NH:10][C:14]2[C:13]([NH:12][C:23]3[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][C:24]=3[Cl:30])=[C:21]([F:22])[C:17]3[N:18]=[CH:19][O:20][C:16]=3[CH:15]=2)(=[O:9])=[O:8])[CH2:6][CH2:5]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 23668039Potassium trimethylsilanolateHCID 897054527-((1-allylcyclopropyl)sulfonyl)-4-fluoro-5-(2-chloro-4-bromophenyl)-5H-imidazo[4',5':4,5]benzo[1,2-d]oxazol-6(7H)-one

Product 1

HCID 897047911-allyl-N-(4-fluoro-5-((4-bromo-2-chlorophenyl)amino)benzo[d]oxazol-6-yl)cyclopropane-1-sulfonamideYield 87.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-((1-allylcyclopropyl)sulfonyl)-4-fluoro-5-(2-chloro-4-bromophenyl)-5H-imidazo[4′,5′:4,5]benzo[1,2-d]oxazol-6(7H)-one (120 mg, 0.23 mmol) in THF (5 mL) was added potassium trimethylsilanolate (32 mg, 0.23 mmol). The mixture was stirred at room temperature for 1 h and treated with saturated NH4Cl (aq.). The aqueous layer was extracted with ethyl acetate (10 mL×2). The combined organic phase was washed with brine (20 mL), dried over Na2SO4, filtered and concentrated to give a residue, which was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate, 5:1-3:1, v/v) to give the product as a white solid (100 mg, 87.6% yield). 1H NMR (400 MHz, CDCl3): δ 8.09 (s, 1H), 7.99 (s, 1H), 7.42 (d, 1H), 7.31-7.25 (m, 1H), 6.80 (s, 1H), 6.43-6.35 (m, 1H), 6.21 (s, 1H), 5.85-5.70 (m, 1H), 5.22-5.14 (m, 2H), 2.83 (d, 2H), 1.28-1.20 (m, 2H), 0.87-0.80 (m, 2H).

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate (10 mL×2)
  2. washThe combined organic phase was washed with brine (20 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a residue, which
  7. customwas purified by flash chromatography on silica gel (petroleum ether/ethyl acetate, 5:1-3:1

Sources & evidence

ORD record
ord-a0f6d292ddcc4062a80589c29291e515
Source dataset
uspto-grants-2016_03
Patent number
US09290468B2

Reaction notes

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