Ammonium Chloride → 4-[4-(2,2-Dioxido-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazin-9-yl)phenoxy]phenol

HRID 1622809Notes

Reaction equation

HRID 1622809 reaction equation
[Si]([O:8][C:9]1[CH:33]=[CH:32][C:12]([O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[C:25]4=[N:26][S:27](=[O:31])(=[O:30])[CH2:28][CH2:29][N:24]4[CH:23]=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[NH4+].[Cl-]>C1COCC1>[O:31]=[S:27]1(=[O:30])[CH2:28][CH2:29][N:24]2[CH:23]=[CH:22][CH:21]=[C:20]([C:17]3[CH:18]=[CH:19][C:14]([O:13][C:12]4[CH:32]=[CH:33][C:9]([OH:8])=[CH:10][CH:11]=4)=[CH:15][CH:16]=3)[C:25]2=[N:26]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 667481279-[4-(4-{[Tert-butyl(dimethyl)silyl]oxy}phenoxy)phenyl]-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

Product 1

HCID 668239904-[4-(2,2-Dioxido-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazin-9-yl)phenoxy]phenolYield 35.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 9-[4-(4-{[tert-butyl(dimethyl)silyl]oxy}phenoxy)phenyl]-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide (1.82 g) in THF (dry) (55 mL) was added to tetrabutylammonium fluoride (1 M in THF) (6.79 mL) at room temperature. After stirring for 0.5 hr, the mixture was added with sat. NH4Cl aq. and silica gel, then concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane then MeOH in EtOAc), recrystallized from THF-IPE, then preparative HPLC (C18, eluent; H2O/MeCN with 0.1% TFA). The collected fraction was concentrated in vacuo. The residue was recrystallized from MeCN—H2O to give the title compound (492 mg) as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by column chromatography (silica gel
  3. washeluted with EtOAc in hexane
  4. customMeOH in EtOAc), recrystallized from THF-IPE
  5. concentrationThe collected fraction was concentrated in vacuo
  6. customThe residue was recrystallized from MeCN—H2O

Sources & evidence

ORD record
ord-a88eec90ee194b88a6ba03179fbf183a
Source dataset
uspto-grants-2014_07
Patent number
US08778934B2

Reaction notes

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