1,2-Dichloroethane → HCID 136348380, compound

HRID 1777074Notes

Reaction equation

HRID 1777074 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([S:7]([C:10]2[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=2)[C:13]([OH:15])=O)(=[O:9])=[O:8])[CH2:3][CH2:2]1.N1(O)C2C=CC=CC=2N=N1.C(Cl)CCl.C(=O)(O)[O-].[Na+].[Cl:38][C:39]1[CH:44]=[CH:43][C:42]([OH:45])=[C:41]([C:46]2[CH:50]=[CH:49][NH:48][N:47]=2)[CH:40]=1>C1COCC1>[Cl:38][C:39]1[CH:44]=[CH:43][C:42]([OH:45])=[C:41]([C:46]2[CH:50]=[CH:49][N:48]([C:13]([C:12]3[CH:16]=[CH:17][CH:18]=[C:10]([S:7]([N:4]4[CH2:3][CH2:2][O:1][CH2:6][CH2:5]4)(=[O:8])=[O:9])[CH:11]=3)=[O:15])[N:47]=2)[CH:40]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 2574763-(Morpholine-4-sulfonyl)benzoic acidHCID 516892Sodium BicarbonateHCID 1785160624-Chloro-2-(1H-pyrazol-3-yl)phenol

Product 1

HCID 136348380HCID 136348380, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(morpholinosulfonyl)benzoic acid (50 mg, 0.184 mmol), 1H-benzo[d][1,2,3]triazol-1-ol (37.4 mg, 0.276 mmol), EDC (53.0 mg, 0.276 mmol) and Sodiumbicarbonate (17.03 mg, 0.203 mmol) was dissolved in THF (10 mL) and then 4-chloro-2-(1H-pyrazol-3-yl)phenol (35.9 mg, 0.184 mmol) was added at room temperature and reaction mixture was allowed to stirred for overnight at room temperature. Reaction was monitored by TLC. After completion of the reaction, the solvent was removed by vacuum and the resulting crude material was purified by flash column chromatography (2% CH3OH/CH2Cl2) afforded the title compound (3-(5-chloro-2-hydroxyphenyl)-1H-pyrazol-1-yl)(3-(morpholinosulfonyl)phenyl)methanone (43 mg, 0.094 mmol, 51.0% yield) as a solid. 1HNMR (400 MHz, CDCl3): δ 8.68 (s, 1H), 8.39 (d, 1H, J=7.6 Hz), 8.01 (d, 1H, J=7.6 Hz), 7.80 (d, 1H, J=2.4 Hz), 7.70 (t, 1H, J=7.6 Hz), 7.53 (d, 1H, J=2.4 Hz), 7.38 (dd, 1H, J=2.4 & 8.4 Hz), 7.27 (d, 1H, J=8.4 Hz), 6.52 (s, 1H), 3.75 (m, 4H), 3.05 (m, 4H). ESI-MS: 448.0 [M+H]+

Workup

  1. customreaction mixture
  2. customReaction
  3. customAfter completion of the reaction
  4. customthe solvent was removed by vacuum
  5. customthe resulting crude material was purified by flash column chromatography (2% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-eda664f5cdd949229764058cf9ba090b
Source dataset
uspto-grants-2016_02
Patent number
US09266838B2

Reaction notes

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