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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Potassium thiocyanate → (R)-N-benzyl-N-(2-(3-(6,8-difluorochroman-3-yl)-2-thioxo-2,3-dihydro-1H-imidazol-4-yl)ethyl)-2-nitrobenzenesulfonamide

HRID 526725
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HRID 526725 반응식
O[C@H]([C@@H](O)C(O)=O)C(O)=O.[F:11][C:12]1[CH:13]=[C:14]2[C:19](=[C:20]([F:22])[CH:21]=1)[O:18][CH2:17][C@H:16]([NH2:23])[CH2:15]2.[CH2:24]([N:31]([CH2:44][CH2:45][C:46](=O)[CH2:47]O)[S:32]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[N+:41]([O-:43])=[O:42])(=[O:34])=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[S-:50][C:51]#[N:52].[K+].C(=O)(O)[O-].[Na+]>C(O)(=O)C.CC(O)C.O.C(O)C>[CH2:24]([N:31]([CH2:44][CH2:45][C:46]1[N:23]([C@@H:16]2[CH2:15][C:14]3[C:19](=[C:20]([F:22])[CH:21]=[C:12]([F:11])[CH:13]=3)[O:18][CH2:17]2)[C:51](=[S:50])[NH:52][CH:47]=1)[S:32]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[N+:41]([O-:43])=[O:42])(=[O:34])=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1
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참가 물질

9

반응물 4

HCID 516872Potassium thiocyanateHCID 516892Sodium BicarbonateHCID 25118723(R)-6,8-difluorochroman-3-amine (2R,3R)-2,3-dihydroxysuccinateHCID 71152063N-benzyl-2-nitro-N-(4-hydroxy-3-oxobutyl)benzenesulfonamide2회

생성물 1

HCID 71152068(R)-N-benzyl-N-(2-(3-(6,8-difluorochroman-3-yl)-2-thioxo-2,3-dihydro-1H-imidazol-4-yl)ethyl)-2-nitrobenzenesulfonamide
수율 64%

시약·촉매·용매 4

HCID 176Acetic Acid용매HCID 702Ethanol용매HCID 962Water용매HCID 3776Isopropanol용매

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온도
100 °C

실험 절차

To a mixture of (R)-6,8-difluorochroman-3-amine(2R,3R)-2,3-dihydroxysuccinate (compound JT′, 1.7 g, 5.07 mmol), N-benzyl-N-(4-hydroxy-3-oxobutyl)-2-nitrobenzenesulfonamide (compound I, 2.303 g, 6.08 mmol) in acetic acid (12.5 ml) was added potassium thiocyanate (0.591 g, 6.08 mmol) in one portion. The mixture was heated with stirring at 100° C. for 3 hours under HPLC control, cooled to 20° C., diluted with 2-propanol (55 ml), cooled to 0° C., aged for 1 hour. The precipitate collected, washed with cold 2-propanol (55 ml), dried to give 12.54 g. The solid was suspended in a mixture of water (38 ml) and ethanol (EtOH) (19 ml), solid sodium bicarbonate (2.255 g, 26.8 mmol) was added in portions with stirring at 20-25° C., stirred for 30 min. Solid collected, washed with water, dried to give (R)—N-benzyl-N-(2-(3-(6,8-difluorochroman-3-yl)-2-thioxo-2,3-dihydro-1H-imidazol-4-yl)ethyl)-2-nitrobenzenesulfonamide (compound K′, 8.4 g, 14.32 mmol, 64.0% yield).

후처리

  1. temperatureThe mixture was heated
  2. temperaturecooled to 20° C.
  3. temperaturecooled to 0° C.
  4. waitaged for 1 hour
  5. customThe precipitate collected
  6. washwashed with cold 2-propanol (55 ml)
  7. customdried
  8. customto give 12.54 g
  9. additionwas added in portions
  10. stirringwith stirring at 20-25° C.
  11. stirringstirred for 30 min
  12. customSolid collected
  13. washwashed with water
  14. customdried

출처 및 근거

ORD 기록
ord-ec3999171d0f43b2a28f78f2420ddff4
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09346751B2

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