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Pyridine → N-[(4aR,6R,8aS)-8a-(5-cyano-2-fluorophenyl)-6-cyclopropyl-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide

HRID 2168306
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HRID 2168306 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([F:31])=[C:6]([C@@:8]2([NH:19][C:20]([NH:22][C:23](=[O:30])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[S:21])[C@H:13]([CH2:14]O)[CH2:12][C@H:11]([CH:16]3[CH2:18][CH2:17]3)[O:10][CH2:9]2)[CH:7]=1.[N:32]1C=CC=C[CH:33]=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O>ClCCl>[C:33]([C:2]1[CH:3]=[CH:4][C:5]([F:31])=[C:6]([C@:8]23[CH2:9][O:10][C@@H:11]([CH:16]4[CH2:18][CH2:17]4)[CH2:12][C@H:13]2[CH2:14][S:21][C:20]([NH:22][C:23](=[O:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:19]3)[CH:7]=1)#[N:32]
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참가 물질

5

반응물 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 86721310N-{[(3S,4R,6R)-3-(5-bromo-2-fluorophenyl)-6-cyclopropyl-4-(hydroxymethyl)tetrahydro-2H-pyran-3-yl]carbamothioyl}benzamide

생성물 1

HCID 86762667N-[(4aR,6R,8aS)-8a-(5-cyano-2-fluorophenyl)-6-cyclopropyl-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매
2회

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온도
0 °C

실험 절차

A solution of N-{[(3S,4R,6R)-3-(5-bromo-2-fluorophenyl)-6-cyclopropyl-4-(hydroxymethyl)tetrahydro-2H-pyran-3-yl]carbamothioyl}benzamide (C57) (127 mg, 0.28 mmol) and pyridine (81 μL, 1.01 mmol) in dichloromethane (12 mL) was cooled to −50° C. Trifluoromethanesulfonic anhydride (94 μL, 0.56 mmol) was added drop-wise to the solution and the mixture was gradually warmed to 0° C. over 90 minutes. The reaction mixture was diluted with dichloromethane (20 mL), washed with water (2×30 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 100% ethyl acetate in heptane) afforded the product as a solid. Yield: 83 mg, 68%. LCMS m/z 436.2 [M+H+].

후처리

  1. washwashed with water (2×30 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification via silica gel chromatography (Gradient: 0% to 100% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-0a44ffe2c8be472a825fd985f30454a9
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09045498B2

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