Propiolic Acid → N-{1-[(2S)-2-((3S)-3-{[(6-Chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoyl]piperidin-3-yl}prop-2-ynamide

HRID 7303

Reaction equation

HRID 7303 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8](=[O:32])[C@@H:9]([N:11]2[CH2:15][CH2:14][C@H:13]([NH:16][S:17]([C:20]3[CH:29]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[C:25]([Cl:30])[CH:26]=4)[CH:21]=3)(=[O:19])=[O:18])[C:12]2=[O:31])[CH3:10])[CH2:3]1.[C:33](O)(=[O:36])[C:34]#[CH:35].C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Cl:30][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][CH:24]=1)[CH:21]=[C:20]([S:17]([NH:16][C@H:13]1[CH2:14][CH2:15][N:11]([C@@H:9]([CH3:10])[C:8]([N:4]3[CH2:5][CH2:6][CH2:7][CH:2]([NH:1][C:33](=[O:36])[C:34]#[CH:35])[CH2:3]3)=[O:32])[C:12]1=[O:31])(=[O:19])=[O:18])[CH:29]=[CH:28]2

Participants

6

Reactant 4

HCID 10110Propiolic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69329851N-((3S)-1-[(1S)-2-(3-aminopiperidin-1-yl)-1-methyl-2-oxoethyl]-2-oxopyrrolidin-3-yl)-6-chloronaphthalene-2-sulfonamide

Product 1

HCID 10165402N-{1-[(2S)-2-((3S)-3-{[(6-Chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoyl]piperidin-3-yl}prop-2-ynamideYield 115.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-{(3S)-1-[(1S)-2-(3-aminopiperidin-1-yl)-1-methyl-2-oxoethyl]-2-oxopyrrolidin-3-yl}-6-chloronaphthalene-2-sulfonamide (0.005 g) in DMF (0.5 ml) were added propiolic acid (0.001 g), N,N-diisopropylethylamine (0.0044 ml) and o-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.004 g). The mixture was stirred at room temperature for 18 h and then concentrated under reduced pressure. The residue was partitioned between DCM and saturated sodium bicarbonate solution and then passed through a hydrophobic frit. The separated organic fraction was concentrated under reduced pressure to give the title compound (0.0064 g) as an oil.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between DCM and saturated sodium bicarbonate solution
  3. concentrationThe separated organic fraction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-735af55b970e46e6a71764fc75e55f39
Source dataset
uspto-grants-2006_08
Patent number
US07084139B2

Linked notes

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