Methanesulfonamide → HCID 67036337, compound

HRID 1623494Notes

Reaction equation

HRID 1623494 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:21][C:22]3[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=3)[C:25](O)=[O:26])[C:13]2=[O:31])[CH:9]([CH3:11])[CH3:10])=[CH:4][CH:3]=1.Cl.CN(C)CCCN=C=NCC.[CH3:44][S:45]([NH2:48])(=[O:47])=[O:46]>CN(C1C=CN=CC=1)C.ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:21][C:22]3[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=3)[C:25]([NH:48][S:45]([CH3:44])(=[O:47])=[O:46])=[O:26])[C:13]2=[O:31])[CH:9]([CH3:10])[CH3:11])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67036258HCID 67036258, compound

Product 1

HCID 67036337HCID 67036337, compoundYield 38.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-{3-[1-(4-chloro-phenyl)-2-methyl-propylidene]-2-oxo-2,3-dihydro-indol-1-ylmethyl}-benzoic acid (0.22 g, 0.51 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.20 g, 1.02 mmol), methylsulfonamide (97 mg, 1.02 mmol), DMAP (12.2 mg, 0.10 mmol) in dichloromethane (20 ml) was stirred for 72 hours. The organic solution washed with brine (10 ml) then dried over sodium sulfate. After removal of solvent, the residue was dissolved in 2 ml DMF for prepared HPLC to give the product N-(3-{3-[1-(4-chloro-phenyl)-2-methyl-propylidene]-2-oxo-2,3-dihydro-indol-1-ylmethyl}-benzoyl)-methanesulfonamide (100 mg, 38%) as yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.21 (d, J=6.82 Hz, 6H) 3.50 (s, 3H) 5.00-5.12 (m, 1H) 5.17 (s, 2H) 5.52 (s, 1H) 5.84 (d, J=7.83 Hz, 1H) 6.75 (t, J=7.83 Hz, 1H) 6.85 (d, J=7.83 Hz, 1H) 7.17 (t, J=7.20 Hz, 1H) 7.28 (d, J=8.59 Hz, 2H) 7.60 (t, J=7.71 Hz, 1H) 7.65 (d, J=8.34 Hz, 2H) 7.70 (d, J=7.83 Hz, 1H) 7.94 (d, J=7.83 Hz, 1H) 8.02 (s, 1H). MS calcd. for C27H25ClN2O4S 508.5, obsd. (ESI+) [(M+H)+] 509.2.

Workup

  1. washThe organic solution washed with brine (10 ml)
  2. dry with materialthen dried over sodium sulfate
  3. customAfter removal of solvent
  4. dissolutionthe residue was dissolved in 2 ml DMF
  5. customfor prepared HPLC

Sources & evidence

ORD record
ord-a02986c1cc3444f0acf92dab5b7b2dd6
Source dataset
uspto-grants-2014_07
Patent number
US08778973B2

Reaction notes

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