5-(2-Pyridyl)thiophene-2-sulfonyl chloride → HCID 59463114, compound

HRID 1712957Notes

Reaction equation

HRID 1712957 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH2:11][CH:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[OH:18])[NH:9][N:8]=2)[CH:2]=1.[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]1[S:29][C:28]([S:30](Cl)(=[O:32])=[O:31])=[CH:27][CH:26]=1>N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH2:11][CH:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[OH:18])[N:9]([S:30]([C:28]3[S:29][C:25]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][N:19]=4)=[CH:26][CH:27]=3)(=[O:31])=[O:32])[N:8]=2)[CH:2]=1

Participants

5

Reactant 2

HCID 27372315-(2-Pyridyl)thiophene-2-sulfonyl chlorideHCID 226963962-(3-pyridin-3-yl-4,5-dihydro-1H-pyrazol-5-yl)phenol

Product 1

HCID 59463114HCID 59463114, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To 2-(3-pyridin-3-yl-4,5-dihydro-1H-pyrazol-5-yl)phenol (29.85 mg, 0.1149 mmol) placed in a sealed tube was added a solution of 5-pyridin-2-ylthiophene-2-sulfonyl chloride (29.85 mg, 0.1045 mmol) in pyridine (0.5 mL). The reaction mixture was shaken at rt for 18 h. The reaction mixture was diluted with a saturated solution of sodium bicarbonate (2.0 mL) and extracted with DCM. The organic solutions were combined, dried over MgSO4, filtered, and concentrated. The residue was purified by RP-HPLC to give 2-{3-pyridin-3-yl-1-[(5-pyridin-2-yl-2-thienyl)sulfonyl]-4,5-dihydro-1H-pyrazol-5-yl}phenol (I-126) (14.50 mg, 30.0%). 1H NMR (300 MHz, d6-DMSO) δ: 9.77 (s, 1H), 8.87 (bd, 1H), 8.64 (dd, 1H), 8.56 (bd, 1H), 8.12 (dt, 1H), 8.03 (d, 1H), 7.87-7.92 (m, 2H), 7.72 (d, 1H), 7.48 (dd, 1H), 7.35-7.40 (m, 2H), 7.11-7.17 (m, 1H), 6.81-6.85 (m, 2H), 5.24 (dd, 1H), 3.74 (dd, 1H), and 3.20 (dd, 1H). LCMS: (FA) ES+ 463.0, ES-460.9.

Workup

  1. extractionextracted with DCM
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-f38d18fe2bba44a2b1a71c7a18b1bcb1
Source dataset
uspto-grants-2010_09
Patent number
US07795249B2

Reaction notes

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