Methanesulfonamide → HCID 22405584, compound

HRID 441192Notes

Reaction equation

HRID 441192 reaction equation
[C:1]([C:4]1[CH:41]=[CH:40][C:7]([CH2:8][O:9][C:10]([NH:12][C:13]2[C:14](=[O:39])[N:15]([CH2:25][C:26]([NH:28][CH:29]([CH:36]([CH3:38])[CH3:37])[C:30](=[O:35])[C:31]([F:34])([F:33])[F:32])=[O:27])[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:17][CH:18]=2)=[O:11])=[CH:6][CH:5]=1)(O)=[O:2].Cl.CN(C)CCCN=C=NCC.[CH3:54][S:55]([NH2:58])(=[O:57])=[O:56]>CN(C)C1C=CN=CC=1.ClCCl.C(OCC)(=O)C>[CH3:54][S:55]([NH:58][C:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10]([NH:12][C:13]2[C:14](=[O:39])[N:15]([CH2:25][C:26]([NH:28][CH:29]([CH:36]([CH3:37])[CH3:38])[C:30](=[O:35])[C:31]([F:33])([F:34])[F:32])=[O:27])[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:17][CH:18]=2)=[O:11])=[CH:40][CH:41]=1)=[O:2])(=[O:57])=[O:56]

Participants

7

Reactant 3

HCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10076806HCID 10076806, compound

Product 1

HCID 22405584HCID 22405584, compound

Reagents, catalysts & solvents 3

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

Procedure

To a solution of 2-[3-(4-carboxybenzyloxycarbonylamino)-2-oxo-6-phenyl-1,2-dihydro-1-pyridyl]-N-(3,3,3-trifluoro-1-isopropyl-2-oxopropyl)acetamide (0.387 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.43 g) and 4-dimethylaminopyridine (0.27 g) in dry dichloromethane was added methanesulfonamide; and the reaction mixture was stirred for 5 days. The mixture was diluted with ethyl acetate, washed (three times with 10% aqueous hydrochloric acid, then brine), dried and evaporated before purification by chromatography, eluting with dichloromethane:ethyl acetate:methanol:acetic acid (50:48.9:1.0:0.1), to give the title compound; TLC: Rf =0.38, dichloromethane:ethyl acetate:methanol:acetic acid (50:48.9:1.0:0.1); HPLC: tR =5.38, FR=2, column A, water:acetonitrile (7:3); MS: m/z=651(M+1).

Workup

  1. washwashed (three times with 10% aqueous hydrochloric acid
  2. dry with materialbrine), dried
  3. customevaporated before purification by chromatography
  4. washeluting with dichloromethane:ethyl acetate:methanol:acetic acid (50:48.9:1.0:0.1)

Sources & evidence

ORD record
ord-2da05d5e805f44b49706e645770a379e
Source dataset
uspto-grants-1996_05
Patent number
US05521179

Reaction notes

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