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Trifluoroacetic acid → HCID 59580663, 화합물

HRID 533319
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HRID 533319 반응식
[F:1][C:2]1[N:3]=[C:4]([C:22]2[CH:23]=[N:24][CH:25]=[C:26]([F:28])[CH:27]=2)[S:5][C:6]=1[N:7](C(OC(C)(C)C)=O)[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].FC(F)(F)C(O)=O>ClCCl>[C:11]([O:10][C:8](=[O:9])[NH:7][C:6]1[S:5][C:4]([C:22]2[CH:23]=[N:24][CH:25]=[C:26]([F:28])[CH:27]=2)=[N:3][C:2]=1[F:1])([CH3:14])([CH3:12])[CH3:13]
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참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 59580494HCID 59580494, 화합물

생성물 1

HCID 59580663HCID 59580663, 화합물수율 68.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of di(tert-butyl) 4-fluoro-2-(5-fluoropyridin-3-yl)-1,3-thiazol-5-ylimidodicarbonate (320 mg, 0.77 mmol) in DCM (7 mL) was added trifluoroacetic acid (TFA) (0.7 mL). The solution was stirred at room temperature for 10 minutes, before quenched slowly with saturated NaHCO3 solution. The organic layer was separated and the aqueous layer was extracted with dichloromethane (DCM). The combined organic layer was dried over Na2SO4, filtered and purified by silica gel chromatography (0 to 100% ethyl acetate/hexanes) to give product as a pale yellow solid (166 mg, 68%): mp 188-191° C.; 1H NMR (300 MHz, CDCl3) δ 8.84 (s, 1H), 8.46 (d, J=2.7 Hz, 1H), 7.85 (ddd, J=9.1, 2.6, 1.7 Hz, 1H), 6.92 (br s, 1H), 1.55 (s, 9H); ESIMS m/z 312 (M−1).

후처리

  1. custombefore quenched slowly with saturated NaHCO3 solution
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with dichloromethane (DCM)
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. custompurified by silica gel chromatography (0 to 100% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-226bc2d3d5d44e99ba886556ee463374
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08853246B2

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