Tetrabutylammonium Fluoride → HCID 21186225, compound

HRID 361433Notes

Reaction equation

HRID 361433 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[O:19]([CH2:27][CH:28]([CH3:55])[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[C:41]([S:42]([NH:45][C:46]3[C:51]([O:52][CH3:53])=[N:50][C:49]([CH3:54])=[CH:48][N:47]=3)(=[O:44])=[O:43])=[CH:40][CH:39]=[CH:38][N:37]=2)=[CH:32][CH:31]=1)[Si](C(C)(C)C)(C)C>C1COCC1.O>[OH:19][CH2:27][CH:28]([CH3:55])[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[C:41]([S:42]([NH:45][C:46]3[C:51]([O:52][CH3:53])=[N:50][C:49]([CH3:54])=[CH:48][N:47]=3)(=[O:44])=[O:43])=[CH:40][CH:39]=[CH:38][N:37]=2)=[CH:32][CH:31]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride2×HCID 21186331HCID 21186331, compound

Product 1

HCID 21186225HCID 21186225, compoundYield 80.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Tetrabutylammonium fluoride (0.4 ml of a 1.0M solution in THF) was added to a solution of 2-[4-(2-((tert-butyldimethylsiloxy)methyl)propyl)phenyl]-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (118 mg) in THF (5 ml) at ambient temperature. More tetrabutylammonium fluoride solution was added after 0.25 hour (0.4 ml), after 0.75 hour (1.0 ml) and finally after 1.5 hours (0.2 ml). The reaction mixture was stirred for a further 0.5 hour, diluted with water (10 ml) and the reaction mixture was extracted with dichloromethane (4×10 ml). The combined organic extracts were dried over MgSO4 and evaporated to give an amber oil. This was purified by gradient elution with 0-50% methanol/dichloromethane through a silica gel Mega Bond Elut column to give 2-[4-(3-hydroxy-2-methylpropyl)phenyl]-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (75 mg) as a white crystalline solid, m.p.118°-119° C.; 1H NMR (DMSO-d6): 0.95 (d, 3 H), 1.35 (m, 1 H), 2.0 (m, 1 H), 2.3 (s, 3 H), 2.5 (m, 1 H), 2.9 (m, 1 H), 3.5 (m, 2 H), 3.8 (s, 3 H), 6.65 (s, 1 H), 7.2 (m, 4 H), 7.35 (s, 1 H), 7.5 (m, 1 H), 8.7 (d, 1 H), 8.8 (dd, 1 H); mass spectrum (+ve ESP): 429 (M+H)+.

Workup

  1. waitfinally after 1.5 hours (0.2 ml)
  2. extractionthe reaction mixture was extracted with dichloromethane (4×10 ml)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. customevaporated
  5. customto give an amber oil
  6. customThis was purified by gradient elution with 0-50% methanol/dichloromethane through a silica gel Mega Bond Elut column

Sources & evidence

ORD record
ord-8c97a0a6925b45ac924b0ccf3cc695e9
Source dataset
uspto-grants-1999_02
Patent number
US05866568

Reaction notes

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