Benzenesulfonamide → N-[4-[6-(Cyclopentyloxycarbonyl)amino-2,3-dihydrobenz-1,4-oxazin-4ylmethyl]-3-methoxybenzoyl]benzenesulphonamide

HRID 1646346Notes

Reaction equation

HRID 1646346 reaction equation
[C:1]1([S:7]([NH2:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:11]1([O:16][C:17]([NH:19][C:20]2[CH:21]=[CH:22][C:23]3[O:28][CH2:27][CH2:26][N:25]([CH2:29][C:30]4[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][C:31]=4[O:39][CH3:40])[C:24]=3[CH:41]=2)=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12]1.Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.ClCCl>[CH:11]1([O:16][C:17]([NH:19][C:20]2[CH:21]=[CH:22][C:23]3[O:28][CH2:27][CH2:26][N:25]([CH2:29][C:30]4[CH:38]=[CH:37][C:33]([C:34]([NH:10][S:7]([C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)(=[O:9])=[O:8])=[O:35])=[CH:32][C:31]=4[O:39][CH3:40])[C:24]=3[CH:41]=2)=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 7370BenzenesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 147631294-[6-(Cyclopentyloxycarbonyl)amino-2,3-dihydrobenz-1,4-oxazin-4-ylmethyl]-3-methoxybenzoic acid

Product 1

HCID 14763130N-[4-[6-(Cyclopentyloxycarbonyl)amino-2,3-dihydrobenz-1,4-oxazin-4ylmethyl]-3-methoxybenzoyl]benzenesulphonamideYield 54%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Benzenesulphonamide (0.037 g.) was added to a stirred solution of 4-[6-(cyclopentyloxycarbonyl)amino-2,3-dihydrobenz-1,4-oxazin-4-ylmethyl]-3-methoxybenzoic acid (0.1 g.), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.046 g.) and 4-(dimethylamino)pyridine (0.029 g.) in dichloromethane (5 ml.), under an atmosphere of nitrogen. The mixture was stirred for 21 hours and then diluted with dichloromethane. This mixture was washed successively with 1M hydrochloric acid (2×10 ml.), 5% w/v sodium bicarbonate solution (2×10 ml.), and saturated brine (20 ml.). It was then dried (MgSO4) and evaporated. The residue was purified by flash chromatography on silica gel (3 cm. diameter column) eluting with 1:1 v/v ethyl acetate:hexane. The solid obtained was recrystallized from ethyl acetate to give the title compound as a white powder (0.071 g., 54%), m.p. 186°-187° C.

Workup

  1. washThis mixture was washed successively with 1M hydrochloric acid (2×10 ml.), 5%
  2. dry with materialIt was then dried (MgSO4)
  3. customevaporated
  4. customThe residue was purified by flash chromatography on silica gel (3 cm. diameter column)
  5. washeluting with 1:1 v/v ethyl acetate
  6. customThe solid obtained
  7. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-fed14f260ead4dbaa636e0236fe74961
Source dataset
uspto-grants-1993_01
Patent number
US05179112

Reaction notes

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