1427081-05-7 → HCID 89500346, compound

HRID 925440Notes

Reaction equation

HRID 925440 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1[CH2:9][O:10][CH2:11][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[CH:16]=2)([CH3:14])[N:13]=1)([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[Br:28][C:29]1[CH:38]=[CH:37][C:32]2[C:33](Cl)=[N:34][S:35][C:31]=2[CH:30]=1>C1COCC1>[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1[CH2:9][O:10][CH2:11][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][C:33]3[C:32]4[CH:37]=[CH:38][C:29]([Br:28])=[CH:30][C:31]=4[S:35][N:34]=3)[CH:16]=2)([CH3:14])[N:13]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 571960831427081-05-7HCID 66666030[5-(3-Amino-phenyl)-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-carbamic acid tert-butyl esterHCID 178418339Butyllithium

Product 1

HCID 89500346HCID 89500346, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of [5-(3-amino-phenyl)-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-carbamic acid tert-butyl ester (51 mg, 0.167 mmol) in THF (2 ml) was stirred at −78° C. under nitrogen. Butyllithium (1.6 M solution in hexanes, 0.26 ml, 0.418 mmol) was added at once. After 10 minutes a solution of 6-bromo-3-chloro-benzo[d]isothiazole (WO 2006091858, page 132; 52 mg, 0.209 mmol) in 0.4 ml THF was added rapidly. After stirring for 30 minutes the mixture was quenched with 5% aq. NH4Cl and warmed to rt. The mixture was extracted with EtOAc, and the organic phase was washed with brine, dried with Na2SO4 and evaporated under reduced pressure. The residue was purified by chromatography on silica gel (hexanes/20-35% EtOAc) to yield the title compound.

Workup

  1. customwas quenched with 5% aq. NH4Cl
  2. extractionThe mixture was extracted with EtOAc
  3. washthe organic phase was washed with brine
  4. dry with materialdried with Na2SO4
  5. customevaporated under reduced pressure
  6. customThe residue was purified by chromatography on silica gel (hexanes/20-35% EtOAc)

Sources & evidence

ORD record
ord-950a4e8320bf4f6a925b140b1fb2ea1f
Source dataset
uspto-grants-2016_03
Patent number
US09284284B2

Reaction notes

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