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6-Bromo-3-chloro-1,2-benzothiazole → {5-[3-(6-Bromo-benzo[d]isothiazol-3-ylamino)-phenyl]-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-yl}-carbamic acid tert-butyl ester

HRID 925440
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HRID 925440 반응식
[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]
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참가 물질

5

반응물 3

HCID 571960836-Bromo-3-chloro-1,2-benzothiazoleHCID 66666030[5-(3-Amino-phenyl)-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-carbamic acid tert-butyl esterHCID 178418339Butyllithium

생성물 1

HCID 89500346{5-[3-(6-Bromo-benzo[d]isothiazol-3-ylamino)-phenyl]-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-yl}-carbamic acid tert-butyl ester

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-950a4e8320bf4f6a925b140b1fb2ea1f
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09284284B2

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