Cesium carbonate → ethyl 6-(N-(5-cyclopropyl-3-(methylcarbamoyl)-2-(p-tolyl)furo[2,3-b]pyridin-6-yl)methylsulfonamido)-2-(methylsulfonyl)hexanoate

HRID 2190198Notes

Reaction equation

HRID 2190198 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]([C:11]1[N:16]=[C:15]2[O:17][C:18]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=3)=[C:19]([C:20]([NH:22][CH3:23])=[O:21])[C:14]2=[CH:13][C:12]=1[CH:31]1[CH2:33][CH2:32]1)[S:7]([CH3:10])(=[O:9])=[O:8].[CH3:34][S:35]([CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])(=[O:37])=[O:36].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH:31]1([C:12]2[CH:13]=[C:14]3[C:19]([C:20](=[O:21])[NH:22][CH3:23])=[C:18]([C:24]4[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=4)[O:17][C:15]3=[N:16][C:11]=2[N:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH:38]([S:35]([CH3:34])(=[O:37])=[O:36])[C:39]([O:41][CH2:42][CH3:43])=[O:40])[S:7]([CH3:10])(=[O:9])=[O:8])[CH2:33][CH2:32]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 78201Ethyl methanesulfonylacetateHCID 545758766-(N-(4-bromobutyl)methylsulfonamido)-5-cyclopropyl-N-methyl-2-(p-tolyl)furo[2,3-b]pyridine-3-carboxamide

Product 1

HCID 58052450ethyl 6-(N-(5-cyclopropyl-3-(methylcarbamoyl)-2-(p-tolyl)furo[2,3-b]pyridin-6-yl)methylsulfonamido)-2-(methylsulfonyl)hexanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To 6-(N-(4-bromobutyl)methylsulfonamido)-5-cyclopropyl-N-methyl-2-(p-tolyl)furo[2,3-b]pyridine-3-carboxamide (4.5 mg, 8.42 μmol) was added ethyl 2-(methylsulfonyl)acetate (1.399 mg, 8.42 μmol) and CESIUM CARBONATE (5.49 mg, 0.017 mmol) and KI (1.398 mg, 8.42 μmol) and DMF Heated at 120° C. 20 min. Added water and extracted with EtOAc. Conc. on vac to oil. Added 3 mL ACN and 1 mL water. Filtered with 0.45μ filter Purified via HPLC C18 40-100% ACN/H2O (0.1% NH4OH) 40 mL/min over 10 min. to give ethyl 6-(N-(5-cyclopropyl-3-(methylcarbamoyl)-2-(p-tolyl)furo[2,3-b]pyridin-6-yl)methylsulfonamido)-2-(methylsulfonyl)hexanoate.

Workup

  1. custom20 min
  2. extractionAdded water and extracted with EtOAc
  3. additionAdded 3 mL ACN and 1 mL water
  4. filtrationFiltered with 0.45μ
  5. filtrationfilter
  6. customPurified via HPLC

Sources & evidence

ORD record
ord-397445e13a724d139134a313b0d180ef
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

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