Tetrabutylammonium Fluoride → HCID 59267497, compound

HRID 1945295Notes

Reaction equation

HRID 1945295 reaction equation
[C:1]1([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:6]=[CH:5][C:4]([C:7]2[C:37]([Cl:38])=[CH:36][C:10]3[N:11](COCC[Si](C)(C)C)[C:12]([O:14][C:15]4[CH:16]=[C:17]([S:21]([NH:24][C:25](=[O:27])[CH3:26])(=[O:23])=[O:22])[CH:18]=[CH:19][CH:20]=4)=[N:13][C:9]=3[CH:8]=2)=[CH:3][CH:2]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:25]([NH:24][S:21]([C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([O:14][C:12]2[NH:11][C:10]3[CH:36]=[C:37]([Cl:38])[C:7]([C:4]4[CH:5]=[CH:6][C:1]([C:39]5[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=5)=[CH:2][CH:3]=4)=[CH:8][C:9]=3[N:13]=2)[CH:16]=1)(=[O:23])=[O:22])(=[O:27])[CH3:26]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68659487HCID 68659487, compound

Product 1

HCID 59267497HCID 59267497, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-({3-[(5-biphenyl-4-yl-6-chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1 H-benzimidazol-2-yl)oxy]phenyl}sulfonyl)acetamide (38 mg, 0.059 mmol) and tetrabutylammonium fluoride (1 M in THF) (0.234 mL) in THF (3 mL) was heated at 80° C. for 2 h. Volatiles were removed and the residue was purified by reverse HPLC eluting with MeCN/water to give the title compound. LC-MS: calculated for C27H20ClN3O4S 517.09, observed m/e 518 (M+H)+ (Rt 3.77 min).

Workup

  1. customVolatiles were removed
  2. customthe residue was purified by reverse HPLC
  3. washeluting with MeCN/water

Sources & evidence

ORD record
ord-6e41c2cd280f4395800802f8fd54d6b5
Source dataset
uspto-grants-2013_03
Patent number
US08394969B2

Reaction notes

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