4-Methoxybenzenesulfonamide → HCID 11692597, compound

HRID 2113697Notes

Reaction equation

HRID 2113697 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]([CH2:14][C:15]3[CH:23]=[CH:22][C:18]([C:19](O)=[O:20])=[CH:17][CH:16]=3)[N:12]=[CH:11][CH:10]=2)=[CH:5][C:4]=1[O:24][C@@H:25]1[CH2:29][CH2:28][O:27][CH2:26]1.Cl.CN(C)CCCN=C=NCC.[CH3:42][O:43][C:44]1[CH:49]=[CH:48][C:47]([S:50]([NH2:53])(=[O:52])=[O:51])=[CH:46][CH:45]=1.C([O-])(O)=O.[Na+]>CN(C)C1C=CN=CC=1.C(OCC)(=O)C.O.C(Cl)Cl>[CH3:42][O:43][C:44]1[CH:45]=[CH:46][C:47]([S:50]([NH:53][C:19](=[O:20])[C:18]2[CH:17]=[CH:16][C:15]([CH2:14][N:13]3[C:9]([C:6]4[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([O:24][C@@H:25]5[CH2:29][CH2:28][O:27][CH2:26]5)[CH:5]=4)=[CH:10][CH:11]=[N:12]3)=[CH:23][CH:22]=2)(=[O:52])=[O:51])=[CH:48][CH:49]=1

Participants

9

Reactant 4

HCID 707894-MethoxybenzenesulfonamideHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68706799HCID 68706799, compound

Product 1

HCID 11692597HCID 11692597, compoundYield 74%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Into a vial was added 4-[(5-{4-methoxy-3-[(3R)-tetrahydrofuran-3-yloxy]phenyl}-1H-pyrazol-1-yl)methyl]benzoic acid (50.0 mg, 0.127 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (30.2 mg, 0.158 mmol), 4-dimethylaminopyridine (19.3 mg, 0.158 mmol), 4-methoxybenzenesulphonamide (29.5 mg, 0.158 mmol) and 2 mL of methylene chloride. The reaction was stirred overnight at room temperature, poured into 10 mL of water and 10 mL of ethyl acetate and the pH of the aqueous layer was adjusted to pH˜6 by adding saturated aqueous NaHCO3. The organic layer was dried over sodium sulfate, filtered and approximately 1 g of silica gel was added and the mixture was evaporated to dryness under reduced pressure. The residue was purified by column chromatography on silica gel using a gradient elution going from 0% to 10% methanol in dichloromethane over 20 minutes to give N-[(4-methoxyphenyl)sulfonyl]-4-[(5-{4-methoxy-3-[(3R)-tetrahydrofuran-3-yloxy]phenyl}-1H-pyrazol-1-yl)methyl]benzamide (53 mg, 74%) as a yellow foam. LC/MS (EI) tR 5.22 (Method C), m/z 564.2 (M++1). 1H NMR (CDCl3 300 MHz) δ 1.8-2.0 (m, 2H); 2.6 (br s, 2H); 3.6 (m, 2H); 3.8 (m, 2H); 3.9 (s, 3H); 4.4 (br s, 1H); 5.2 (s, 2H); 6.3 (s, 1H); 6.4 (s, 1H); 6.9 (m, 3H); 7.2-7.6 (m, 3H); 7.7 (t, 2H); 7.8 (d, 2H); 7.9 (d, 2H).

Workup

  1. dry with materialThe organic layer was dried over sodium sulfate
  2. filtrationfiltered
  3. additionapproximately 1 g of silica gel was added
  4. customthe mixture was evaporated to dryness under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel using
  6. washa gradient elution
  7. waitgoing from 0% to 10% methanol in dichloromethane over 20 minutes

Sources & evidence

ORD record
ord-680cee421fc74d78bbd3c307e4a57ca6
Source dataset
uspto-grants-2008_10
Patent number
US07432266B2

Reaction notes

Loading…