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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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(Diethylamino)sulfur trifluoride → 5-(1-fluorocyclobutyl)-N-[2-(5-methyl-1,2,4-oxadiazol-3-yl)-1-methylsulfonylpropan-2-yl]-4-[(2S)-1,1,1-trifluoropropan-2-yl]oxypyridine-2-carboxamide

HRID 1480203
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HRID 1480203 반응식
O[C:2]1([C:6]2[C:7]([O:28][C@@H:29]([CH3:34])[C:30]([F:33])([F:32])[F:31])=[CH:8][C:9]([C:12]([NH:14][C:15]([C:22]3[N:26]=[C:25]([CH3:27])[O:24][N:23]=3)([CH3:21])[CH2:16][S:17]([CH3:20])(=[O:19])=[O:18])=[O:13])=[N:10][CH:11]=2)[CH2:5][CH2:4][CH2:3]1.CCN(S(F)(F)[F:41])CC>ClCCl>[F:41][C:2]1([C:6]2[C:7]([O:28][C@@H:29]([CH3:34])[C:30]([F:31])([F:32])[F:33])=[CH:8][C:9]([C:12]([NH:14][C:15]([C:22]3[N:26]=[C:25]([CH3:27])[O:24][N:23]=3)([CH3:21])[CH2:16][S:17]([CH3:20])(=[O:18])=[O:19])=[O:13])=[N:10][CH:11]=2)[CH2:3][CH2:4][CH2:5]1
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참가 물질

4

반응물 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 902034235-(1-hydroxycyclobutyl)-N-[1-methyl-1-(5-methyl-1,2,4-oxadiazol-3-yl)-2-methylsulfonyl-ethyl]-4-[(1S)-2,2,2-trifluoro-1-methyl-ethoxy]pyridine-2-carboxamide

생성물 1

HCID 902043215-(1-fluorocyclobutyl)-N-[2-(5-methyl-1,2,4-oxadiazol-3-yl)-1-methylsulfonylpropan-2-yl]-4-[(2S)-1,1,1-trifluoropropan-2-yl]oxypyridine-2-carboxamide수율 44%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

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온도
0 °C

실험 절차

To a solution of 5-(1-hydroxycyclobutyl)-N-[2-(5-methyl-1,2,4-oxadiazol-3-yl)-1-methylsulfonylpropan-2-yl]-4-[(2S)-1,1,1-trifluoropropan-2-yl]oxypyridine-2-carboxamide (example 126e, 21 mg, 41.5 μmol) in dry dichloromethane (200 μl) under an argon atmosphere cooled down to 0° C. was added DAST (10.0 mg, 8.22 μl, 62.2 μmol). The reaction mixture was stirred at 0° C. for 1 h and quenched by addition of a 2M aqueous solution of sodium carbonate. The bi-phasic mixture was stirred for 15 minutes and the organic phase was collected. The organic phase was evaporated down to dryness and the crude material was purified by preparative HPLC to yield the title compound (9.2 mg, 44%). MS (ESI, m/z): 509.5 (M+H+).

후처리

  1. customquenched by addition of a 2M aqueous solution of sodium carbonate
  2. stirringThe bi-phasic mixture was stirred for 15 minutes
  3. customthe organic phase was collected
  4. customThe organic phase was evaporated down to dryness
  5. customthe crude material was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-6ebcf35676fb46f08d6d1acf35091b32
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09409866B2

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