Triethylamine → (3S,3aR)-2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-N-(2-sulfamoylethyl)-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxamide

HRID 505754Notes

Reaction equation

HRID 505754 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:10]2[C@@H:18]([CH:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[C@@H:17]3[C:12]([C:13]4[CH:27]=[CH:26][C:25]([C:28]([OH:30])=O)=[CH:24][C:14]=4[CH2:15][CH2:16]3)=[N:11]2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[NH2:70][CH2:71][CH2:72][S:73]([NH2:76])(=[O:75])=[O:74]>CN(C)C=O.C(#N)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([N:10]2[C@@H:18]([CH:19]3[CH2:20][CH2:21][CH2:22][CH2:23]3)[C@@H:17]3[C:12]([C:13]4[CH:27]=[CH:26][C:25]([C:28]([NH:70][CH2:71][CH2:72][S:73](=[O:75])(=[O:74])[NH2:76])=[O:30])=[CH:24][C:14]=4[CH2:15][CH2:16]3)=[N:11]2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 101263TaurinamideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 46871935PF-03882845

Product 1

HCID 66723212(3S,3aR)-2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-N-(2-sulfamoylethyl)-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxamideYield 8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To a solution of (3S,3aR)-2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylic acid, Example 15 (100 mg, 0.24 mmol) in N,N-dimethylformamide (3 mL) was added 1-hydroxybenzotriazole (48 mg, 0.36 mmol), triethylamine (0.07 mL, 0.48 mmol) and O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium tetrafluoroborate (115 mg, 0.36 mmol). The solution was stirred for fifteen minutes followed by addition of 2-aminoethanesulfonamide (44 mg, 0.36 mmol). The solution was stirred for twenty hours at ambient temperature. The reaction was partitioned between ethyl acetate and water. The organic layer was washed with water and brine and dried over magnesium sulfate. Chromatography (reverse phase, acetonitrile/water) provided (3S,3aR)-2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-N-(2-sulfamoylethyl)-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxamide (yellow solid, 10 mg, 8% yield). LC/MS on 4.6×50 mm C-18 column, tR=5.80 minutes (10 to 90% acetonitrile/water over 6 minutes at 2 mL/minute with detection 254 nm, at 50° C.); ES-MS m/z 526 (M+H).

Workup

  1. stirringThe solution was stirred for twenty hours at ambient temperature
  2. customThe reaction was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-4d6cb10d2d5546b5b4eee9a7795481bf
Source dataset
uspto-grants-2010_08
Patent number
US07781428B2

Reaction notes

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