Triethylamine → 5-Chloro-N-{[3-(4-{[(3-chloropropyl)sulfonyl]amino}phenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}-2-thiophenecarboxamide

HRID 731576Notes

Reaction equation

HRID 731576 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][S:5](Cl)(=[O:7])=[O:6].C(N(CC)CC)C.[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:27][CH:26]([CH2:28][NH:29][C:30]([C:32]3[S:33][C:34]([Cl:37])=[CH:35][CH:36]=3)=[O:31])[O:25][C:24]2=[O:38])=[CH:19][CH:18]=1>ClCCl>[Cl:37][C:34]1[S:33][C:32]([C:30]([NH:29][CH2:28][CH:26]2[O:25][C:24](=[O:38])[N:23]([C:20]3[CH:19]=[CH:18][C:17]([NH:16][S:5]([CH2:4][CH2:3][CH2:2][Cl:1])(=[O:7])=[O:6])=[CH:22][CH:21]=3)[CH2:27]2)=[O:31])=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 154103-Chloropropanesulphonyl chlorideHCID 21070787N-{[3-(4-aminophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}-5-chloro-2-thiophenecarboxamide

Product 1

HCID 210707235-Chloro-N-{[3-(4-{[(3-chloropropyl)sulfonyl]amino}phenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}-2-thiophenecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An ice-cooled solution of 26.4 mg (0.15 mmol) of 3-chloro-1-propanesulphonyl chloride and 0.03 ml (0.2 mmol) of triethylamine in 3.5 ml of absolute dichloromethane is admixed with 35 mg (0.1 mmol) of N-{[3-(4-aminophenyl)-2-oxo-1,3-oxazolidin-5-yl]-methyl}-5-chloro-2-thiophene-carboxamide (from Example 149). After 30 min, ice-cooling is removed and the mixture is stirred at room temperature overnight, and 150 mg (about 5.5 eq.) of PS-trisamine (Argonaut Technologies) and 0.5 ml of dichloromethane are then added. The suspension is stirred gently for 2 h and filtered (the resin is washed with dichloromethane/methanol), and the filtrate is concentrated. The product is purified by preparative RP-HPLC. Yield: 19.6 mg (40% of theory),

Workup

  1. temperatureice-cooling
  2. customis removed
  3. addition150 mg (about 5.5 eq.) of PS-trisamine (Argonaut Technologies) and 0.5 ml of dichloromethane are then added
  4. stirringThe suspension is stirred gently for 2 h
  5. filtrationfiltered (the resin
  6. washis washed with dichloromethane/methanol), and the filtrate
  7. concentrationis concentrated
  8. customThe product is purified by preparative RP-HPLC

Sources & evidence

ORD record
ord-9d19103f931e46e3b68fdbb12ba2231e
Source dataset
uspto-grants-2009_09
Patent number
US07585860B2

Reaction notes

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