1-methyl-1H-pyrazole-4-sulfonyl chloride → tert-Butyl {2-[1-(4-chlorophenyl)cyclobutyl]-2-[3-({methyl[(1-methyl-1H-pyrazol-4-yl)sulfonyl]amino}methyl)phenyl]ethyl}carbamate

HRID 591192Notes

Reaction equation

HRID 591192 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][NH:29][CH3:30])[CH:23]=3)[CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:31][N:32]1[CH:36]=[C:35]([S:37](Cl)(=[O:39])=[O:38])[CH:34]=[N:33]1>ClCCl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][N:29]([CH3:30])[S:37]([C:35]4[CH:34]=[N:33][N:32]([CH3:31])[CH:36]=4)(=[O:39])=[O:38])[CH:23]=3)[CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:20])[CH3:18])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 170247301-methyl-1H-pyrazole-4-sulfonyl chlorideHCID 68077950tert-Butyl (2-[1-(4-chlorophenyl)cyclobutyl]-2-{3-[(methylamino)methyl]phenyl}ethyl)carbamate

Product 1

HCID 56835836tert-Butyl {2-[1-(4-chlorophenyl)cyclobutyl]-2-[3-({methyl[(1-methyl-1H-pyrazol-4-yl)sulfonyl]amino}methyl)phenyl]ethyl}carbamate

Reagents, catalysts & solvents 3

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

Procedure

tert-Butyl (2-[1-(4-chlorophenyl)cyclobutyl]-2-{3-[(methylamino)methyl]phenyl}ethyl)carbamate (35 mg, 0.082 mmol) was dissolved in dichloromethane (0.8 mL). 4-Dimethylaminopyridine (10 mg, 0.082 mmol) and 1-methyl-1H-pyrazole-4-sulfonyl chloride (16 mg, 0.09 mmol) was added. The reaction mixture was stirred at room temperature over night. The reaction mixture was diluted with ethyl acetate (20 ml) and washed with aqueous hydrochloric acid (1 N, 5 ml, twice) and sodium bicarbonate. The organic layer was dried (magnesium sulfate) and concentrated in vacuo. The crude product was purified by preparative thin layer chromatography (silica, ethyl acetate, n-heptane). Yield: 36 mg (0.063 mmol, 77%)

Workup

  1. washwashed with aqueous hydrochloric acid (1 N, 5 ml
  2. dry with materialThe organic layer was dried (magnesium sulfate)
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by preparative thin layer chromatography (silica, ethyl acetate, n-heptane)

Sources & evidence

ORD record
ord-dca7e62cc8f248f3b4e8aeecc4c1aa90
Source dataset
uspto-grants-2016_01
Patent number
US09238619B2

Reaction notes

Loading…