Hydrochloric Acid → 4-((E)-3-Naphthalen-2-yl-acryloyl)-1-(2-pyrrolidin-1-yl-ethyl)-piperazin-2-one
Reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[C:10](=[O:21])[CH2:9]1)=[O:7])(C)(C)C.Cl.C(N(CC)CC)C.[CH:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][C:31]=1/[CH:40]=[CH:41]/C(O)=O.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C)C=O>[CH:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][C:31]=1/[CH:40]=[CH:41]/[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][CH2:19][CH2:20]2)[C:10](=[O:21])[CH2:9]1)=[O:7]Participants
7
Reactant 5
HCID 313Hydrochloric Acid
HCID 8471Triethylamine
HCID 7358353-(Naphth-2-yl)acrylic acid
HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)
HCID 669995983-Oxo-4-(2-pyrrolidin-1-yl-ethyl)-piperazine-1-carboxylic acid tert-butyl ester2×Product 1
Reagents, catalysts & solvents 1
Procedure
3-Oxo-4-(2-pyrrolidin-1-yl-ethyl)-piperazine-1-carboxylic acid tert-butyl ester (intermediate 6; 0.03 g, 0.1 mmol) was treated with a hydrogen chloride solution (4 M in 1,4-dioxane, 1 ml) for 15 minutes after which time the solvent was evaporated. The crude salt was dissolved in N,N-dimethylformamide (0.8 ml) with triethylamine (0.06 ml, 0.4 mmol) and (E)-3-naphthalen-2-yl-acrylic acid (0.02 g, 0.1 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluoro-phosphate (0.04 g, 0.1 mmol) were added. The mixture was shaken for 1 h after which time it was directly purified by preparative HPLC. MS (ISP)=378.6 (M+H)+.
Workup
- customwas evaporated
- additionwere added
- customwas directly purified by preparative HPLC
Sources & evidence
- ORD record
- ord-87986ba071974d8aa9000105241a8cdb
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063042B2
Reaction notes
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