HCID 16753952, compound → HCID 58126883, compound

HRID 1971853Notes

Reaction equation

HRID 1971853 reaction equation
CO[C:3]([C:5]1[N:6]=[C:7]2[N:15]([CH2:16][C:17]([N:19]3[CH2:24][C@@H:23]([CH3:25])[O:22][C@H:21]([CH3:26])[CH2:20]3)=[O:18])[CH:14]=[C:13]([N:27]3[CH2:31][CH2:30][CH2:29][S:28]3(=[O:33])=[O:32])[N:8]2[C:9](=[O:12])[C:10]=1[OH:11])=[O:4].[NH2:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([F:42])=[CH:38][C:37]=1[S:43]([N:46]([CH3:48])[CH3:47])(=[O:45])=[O:44]>CO>[CH3:47][N:46]([CH3:48])[S:43]([C:37]1[CH:38]=[C:39]([F:42])[CH:40]=[CH:41][C:36]=1[CH2:35][NH:34][C:3]([C:5]1[N:6]=[C:7]2[N:15]([CH2:16][C:17]([N:19]3[CH2:20][C@@H:21]([CH3:26])[O:22][C@H:23]([CH3:25])[CH2:24]3)=[O:18])[CH:14]=[C:13]([N:27]3[CH2:31][CH2:30][CH2:29][S:28]3(=[O:33])=[O:32])[N:8]2[C:9](=[O:12])[C:10]=1[OH:11])=[O:4])(=[O:45])=[O:44]

Participants

4

Reactant 2

HCID 16753952HCID 16753952, compoundHCID 131730536HCID 131730536, compound

Product 1

HCID 58126883HCID 58126883, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-[2-((2R,6R)-2,6-Dimethyl-morpholin-4-yl)-2-oxo-ethyl]-3-(1,1-dioxo-1lambda*6*-isothiazolidin-2-yl)-6-hydroxy-5-oxo-1,5-dihydro-imidazo[1,2-a]pyrimidine-7-carboxylic acid methyl ester (30 mg, 0.062 mmol) was dissolved in MeOH (1 mL) and 2-aminomethyl-5-fluoro-N,N-dimethyl-benzenesulfonamide (22 mg, 0.093 mmol) was added. The reaction was heated at reflux for 24 hours then filtered hot and the filtrate concentrated. The product was recrystalised from methanol and ether and isolated (17 mg, 43% yield) as a pale yellow solid.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 24 hours
  3. filtrationthen filtered hot
  4. concentrationthe filtrate concentrated
  5. customThe product was recrystalised from methanol and ether
  6. customisolated (17 mg, 43% yield) as a pale yellow solid

Sources & evidence

ORD record
ord-21de94995d8d4131968f8db9c4fa663b
Source dataset
uspto-grants-2013_04
Patent number
US08431581B2

Reaction notes

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