3-[(2-Fluorophenyl)sulfamoyl]benzoic acid → N-(2-fluorophenyl)-3-[(8aR)-hexahydropyrrolo[1,2-a]pyrazin-2(1H)-ylcarbonyl]benzenesulfonamide

HRID 400496

반응식

HRID 400496 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][S:9]([C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15]([OH:17])=O)(=[O:11])=[O:10].[CH2:21]1[NH:26][CH2:25][CH2:24][N:23]2[CH2:27][CH2:28][CH2:29][C@H:22]12>CN(C)C(=O)C.CC1CCCO1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][S:9]([C:12]1[CH:20]=[CH:19][CH:18]=[C:14]([C:15]([N:26]2[CH2:25][CH2:24][N:23]3[CH2:27][CH2:28][CH2:29][C@@H:22]3[CH2:21]2)=[O:17])[CH:13]=1)(=[O:10])=[O:11]

참가 물질

5

반응물 2

HCID 23180733-[(2-Fluorophenyl)sulfamoyl]benzoic acidHCID 7004239(8aR)-Octahydropyrrolo(1,2-a)pyrazine

생성물 1

HCID 46853381N-(2-fluorophenyl)-3-[(8aR)-hexahydropyrrolo[1,2-a]pyrazin-2(1H)-ylcarbonyl]benzenesulfonamide

시약·촉매·용매 2

HCID 73012-Methyltetrahydrofuran용매2회HCID 31374Dimethylacetamide용매

실험 절차

To a mixture of 3-{[(2-fluorophenyl)amino]sulfonyl}benzoic acid (800 mg, 2.71 mmol) and 2-(3H-[1,2,3]triazolo[4,5-h]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (1133 mg, 2.98 mmol) in N,N-dimethylacetamide (6.5 mL) and 2-methyltetrahydrofuran (19.5 mL) was added (R)-octahydropyrrolo[1,2-a]pyrazine (479 mg, 3.79 mmol). The reaction was stirred at room temperature for 3 hours, diluted with 2-methyltetrahydrofuran (5 mL), and washed with saturated bicarbonate (2×25 mL). The combined aqueous layers were adjusted to pH 7 with buffer and re-extracted with 2-methyltetrahydrofuran (3×15 mL). The combined organic layers were concentrated under reduced pressure. The residue was taken up in ethanol (25 mL) and concentrated to give the title compound.

후처리

  1. washwashed with saturated bicarbonate (2×25 mL)
  2. extractionre-extracted with 2-methyltetrahydrofuran (3×15 mL)
  3. concentrationThe combined organic layers were concentrated under reduced pressure
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-6e4348d19e1f49dea3c43bce0d0e1878
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741899B2

연결된 노트

불러오는 중…