Tetrabutylammonium Fluoride → N-{2-[(2,3-Difluorobenzyl)thio]-6-methoxypyrimidin-4-yl}-3-hydroxyazetidine-1-sulfonamide

HRID 1024983Notes

Reaction equation

HRID 1024983 reaction equation
[Si]([O:18][CH:19]1[CH2:22][N:21]([S:23]([NH:26][C:27]2[CH:32]=[C:31]([O:33][CH3:34])[N:30]=[C:29]([S:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[C:39]([F:43])[C:38]=3[F:44])[N:28]=2)(=[O:25])=[O:24])[CH2:20]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[F:44][C:38]1[C:39]([F:43])=[CH:40][CH:41]=[CH:42][C:37]=1[CH2:36][S:35][C:29]1[N:28]=[C:27]([NH:26][S:23]([N:21]2[CH2:20][CH:19]([OH:18])[CH2:22]2)(=[O:25])=[O:24])[CH:32]=[C:31]([O:33][CH3:34])[N:30]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 536283983-{[tert-butyl(diphenyl)silyl]oxy}-N-{2-[(2,3-difluorobenzyl)thio]-6-methoxypyrimidin-4-yl}azetidine-1-sulfonamide

Product 1

HCID 59558820N-{2-[(2,3-Difluorobenzyl)thio]-6-methoxypyrimidin-4-yl}-3-hydroxyazetidine-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared according to the procedure outlined in example 34 using 3-{[tert-butyl(diphenyl)silyl]oxy}-N-{2-[(2,3-difluorobenzyl)thio]-6-methoxypyrimidin-4-yl}azetidine-1-sulfonamide (the product from step ii) (0.29 g) and 1M solution of tetrabutylammoniumfluoride in THF (5 mL). Purification was by reverse phase HPLC (symmetry as the stationary phase and TFA/acetonitrile as the mobile phase) then triturated with MeOH, Et2O followed by iso-hexane to give the title compound as a white solid. Yield: 40 mg

Workup

  1. customThe title compound was prepared
  2. customPurification
  3. customthen triturated with MeOH, Et2O

Sources & evidence

ORD record
ord-5c9bfb577f174a8cab791a0da0d1af20
Source dataset
uspto-grants-2014_05
Patent number
US08722883B2

Reaction notes

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