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

HRID 400496

Reaction equation

HRID 400496 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 73012-MethyltetrahydrofuranSolvent2×HCID 31374DimethylacetamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6e4348d19e1f49dea3c43bce0d0e1878
Source dataset
uspto-grants-2014_06
Patent number
US08741899B2

Linked notes

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