3-{[(3-Fluorophenyl)amino]sulfonyl}benzoic acid → N-(3-fluorophenyl)-3-[(8aS)-hexahydropyrrolo[1,2-a]pyrazin-2(1H)-ylcarbonyl]benzenesulfonamide

HRID 400499

반응식

HRID 400499 반응식
[F:1][C:2]1[CH:3]=[C:4]([NH:8][S:9]([C:12]2[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=2)[C:15]([OH:17])=O)(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:45]1[NH:50][CH2:49][CH2:48][N:47]2[CH2:51][CH2:52][CH2:53][C@@H:46]12>CN(C)C(=O)C.CC1CCCO1>[F:1][C:2]1[CH:3]=[C:4]([NH:8][S:9]([C:12]2[CH:20]=[CH:19][CH:18]=[C:14]([C:15]([N:50]3[CH2:49][CH2:48][N:47]4[CH2:51][CH2:52][CH2:53][C@H:46]4[CH2:45]3)=[O:17])[CH:13]=2)(=[O:10])=[O:11])[CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 7665363-{[(3-Fluorophenyl)amino]sulfonyl}benzoic acidHCID 781249(6S)-1,4-Diazabicyclo(4.3.0)nonaneHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

생성물 1

HCID 46853382N-(3-fluorophenyl)-3-[(8aS)-hexahydropyrrolo[1,2-a]pyrazin-2(1H)-ylcarbonyl]benzenesulfonamide

시약·촉매·용매 2

HCID 73012-Methyltetrahydrofuran용매3회HCID 31374Dimethylacetamide용매

실험 절차

To 3-{[(3-fluorophenyl)amino]sulfonyl}benzoic acid (0.9 g, 3.05 mmol) and 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (1.27 g, 3.35 mmol) in N,N-dimethylacetamide (6.4 mL) and 2-methyltetrahydrofuran (15 mL) was added (S)-octahydropyrrolo[1,2-a]pyrazine (0.55 g, 4.33 mmol) in 2-methyltetrahydrofuran (4 mL). The reaction was stirred at ambient temperature overnight and then diluted with 2-methyltetrahydrofuran (15 mL). The organic solution was washed with 6% NaHCO3/6% NaCl (10 mL), and the aqueous layer was extracted with 2-methyltetrahydrofuran (15 mL). The combined organic layers were washed with 6% NaHCO3/6% NaCl (10 mL), saturated NaCl (2×10 mL, 2×20 mL) and 1:1 saturated NaCl/water (2×20 mL), and then concentrated. The residue was concentrated from ethanol (2×10 mL) to give the title compound.

후처리

  1. washThe organic solution was washed with 6% NaHCO3/6% NaCl (10 mL)
  2. extractionthe aqueous layer was extracted with 2-methyltetrahydrofuran (15 mL)
  3. washThe combined organic layers were washed with 6% NaHCO3/6% NaCl (10 mL), saturated NaCl (2×10 mL, 2×20 mL) and 1:1 saturated NaCl/water (2×20 mL)
  4. concentrationconcentrated
  5. concentrationThe residue was concentrated from ethanol (2×10 mL)

출처 및 근거

ORD 기록
ord-3076e350e6064c0f99ddcf10cd644fdb
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741899B2

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