1,2-Dichloroethane → 4-(3-Cyclopentyl-indole-1-sulfonyl)-N-(5-fluoro-pyridin-2-yl-methyl)-benzamide

HRID 737067Notes

Reaction equation

HRID 737067 reaction equation
[CH:1]1([C:6]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]([S:15]([C:18]3[CH:26]=[CH:25][C:21]([C:22]([OH:24])=O)=[CH:20][CH:19]=3)(=[O:17])=[O:16])[CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[F:27][C:28]1[CH:29]=[CH:30][C:31]([CH2:34][NH2:35])=[N:32][CH:33]=1.C(Cl)CCl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH:1]1([C:6]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]([S:15]([C:18]3[CH:26]=[CH:25][C:21]([C:22]([NH:35][CH2:34][C:31]4[CH:30]=[CH:29][C:28]([F:27])=[CH:33][N:32]=4)=[O:24])=[CH:20][CH:19]=3)(=[O:16])=[O:17])[CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 45079543(5-Fluoropyridin-2-yl)methanamineHCID 58975136HCID 58975136, compound

Product 1

HCID 589750384-(3-Cyclopentyl-indole-1-sulfonyl)-N-(5-fluoro-pyridin-2-yl-methyl)-benzamideYield 502.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Stir mixture of 4-(3-Cyclopentyl-indole-1-sulfonyl)-benzoic acid (0.767 g, 0.21 m mol), C-(5-fluoro-pyridin-2yl)-methylamine (0.041 g, 0.25 mmol), and EDC (0.063 g, 0.33 mmol) in dry CH2Cl2 (15 mL) under N2 and add DMAP (0.061 g, 0.50 mmol.). Stir the resulting mixture at ambient temperature for 72 h. Dilute the reaction mixture to 50 mL with CH2Cl2, wash with H2O, 1N NaOH, and brine sequentially. Dry the organic layer (MgSO4), filter and evaporate to give 0.189 g of crude product. Chromatograph on the ISCO using a 12 g column and eluting with Hexane-EtOAc (0-100%) to gives the title compound 0.60 g as a foam:

Workup

  1. stirringStir the resulting mixture at ambient temperature for 72 h
  2. washwash with H2O, 1N NaOH, and brine sequentially
  3. dry with materialDry the organic layer (MgSO4)
  4. filtrationfilter
  5. customevaporate
  6. customto give 0.189 g of crude product
  7. washeluting with Hexane-EtOAc (0-100%)

Sources & evidence

ORD record
ord-f5773b0e66b54aa2b92291df7cc98e20
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

Loading…