3-Bromo-5-(trifluoromethyl)benzenesulfonyl chloride → HCID 44611775, compound

HRID 1645150Notes

Reaction equation

HRID 1645150 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][N:6]1[C:14]2[CH2:13][CH2:12][CH2:11][C@@H:10]([NH2:15])[C:9]=2[CH:8]=[N:7]1)[CH3:2].[Br:17][C:18]1[CH:19]=[C:20]([S:28](Cl)(=[O:30])=[O:29])[CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1>O1CCCC1.CN(C)C1C=CN=CC=1>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][N:6]1[C:14]2[CH2:13][CH2:12][CH2:11][C@@H:10]([NH:15][S:28]([C:20]3[CH:21]=[C:22]([C:24]([F:25])([F:26])[F:27])[CH:23]=[C:18]([Br:17])[CH:19]=3)(=[O:30])=[O:29])[C:9]=2[CH:8]=[N:7]1)[CH3:2]

Participants

5

Reactant 2

HCID 27786103-Bromo-5-(trifluoromethyl)benzenesulfonyl chlorideHCID 59152881HCID 59152881, compound

Product 1

HCID 44611775HCID 44611775, compoundYield 73.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of ((R)-4-amino-4,5,6,7-tetrahydro-indazol-1-yl)-acetic acid ethyl ester (446 mg, 2.0 mmol) and 3-bromo-5-trifluoromethyl-benzenesulfonyl chloride (970 mg, 3.0 mmol) in tetrahydrofuran (5 mL) was added a solution of dimethyl-pyridin-4-yl-amine (489 mg, 4.0 mmol) in tetrahydrofuran (5 mL) dropwise. After being stirred at room temperature overnight, the mixture was concentrated. The residue was purified by column chromatography (gradient elution, 0-5% methanol in dichloromethane) to afford [(R)-4-(3-bromo-5-trifluoromethyl-benzenesulfonylamino)-4,5,6,7-tetrahydro-indazol-1-yl]-acetic acid ethyl ester (750 mg, 63.6%) as a white solid. MS calcd. for C18H19BrF3N3O4S 509, obsd. (ESI+) [(M+H)+] 510.

Workup

  1. concentrationthe mixture was concentrated
  2. customThe residue was purified by column chromatography (gradient elution, 0-5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-cd3f8a3d03314bafbeb6023a3cb05601
Source dataset
uspto-grants-2012_02
Patent number
US08124641B2

Reaction notes

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