1,2-Dichloroethane → N-ethyl-6-[4-({[6-(3-fluorophenyl)pyridin-3-yl]carbonyl}amino)piperidin-1-yl]-N-(2-hydroxyethyl)nicotinamide

HRID 602090Notes

Reaction equation

HRID 602090 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[CH:12][C:11]([C:14]([NH:16][CH:17]3[CH2:22][CH2:21][N:20]([C:23]4[CH:31]=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][N:24]=4)[CH2:19][CH2:18]3)=[O:15])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C[N:47]1[CH2:52][CH2:51][O:50][CH2:49][CH2:48]1.C(NCCO)C>O.C(OCC)(=O)C.CC(N(C)C)=O>[CH2:52]([N:47]([CH2:48][CH2:49][OH:50])[C:27](=[O:28])[C:26]1[CH:30]=[CH:31][C:23]([N:20]2[CH2:19][CH2:18][CH:17]([NH:16][C:14]([C:11]3[CH:12]=[N:13][C:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=4)=[CH:9][CH:10]=3)=[O:15])[CH2:22][CH2:21]2)=[N:24][CH:25]=1)[CH3:51]

Participants

9

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 80722-(Ethylamino)ethanolHCID 757711-HydroxybenzotriazoleHCID 597439796-[4-({[6-(3-Fluorophenyl)pyridin-3-yl]carbonyl}amino)piperidin-1-yl]nicotinic acid

Product 1

HCID 59743999N-ethyl-6-[4-({[6-(3-fluorophenyl)pyridin-3-yl]carbonyl}amino)piperidin-1-yl]-N-(2-hydroxyethyl)nicotinamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

To a vial containing 6-[4-({[6-(3-fluorophenyl)pyridin-3-yl]carbonyl}amino)piperidin-1-yl]nicotinic acid (63.07 mg, 0.15 mmol) was added 0.375 mL of DMA, EDC (31.6 mg, 0.16 mmol), HOBt (20.3 mg, 0.15 mmol), NMM (0.04 mL, 0.37 mmol) and 2-(ethylamino)ethanol (13.4 mg, 0.15 mmol). The reaction mixture was stirred at room temperature for 12 hours and then diluted with water and ethyl acetate. The layers were separated and the organic layer collected and concentrated to give an oil, which was purified by RP-HPLC to give N-ethyl-6-[4-({[6-(3-fluorophenyl)pyridin-3-yl]carbonyl}amino)piperidin-1-yl]-N-(2-hydroxyethyl)nicotinamide

Workup

  1. customThe layers were separated
  2. customthe organic layer collected
  3. concentrationconcentrated
  4. customto give an oil, which
  5. customwas purified by RP-HPLC

Sources & evidence

ORD record
ord-e6c05a33448c4fdabfb029296d8240ee
Source dataset
uspto-grants-2011_03
Patent number
US07902373B2

Reaction notes

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