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N,N-Diethyl-2-propanamine → (S)-5-phenyl-N-(1-(pyrrolo[1,2-a]pyrazin-1-yl)pyrrolidin-3-yl)-1,2,4-oxadiazole-3-carboxamide

HRID 1755273
Notes
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Reaction equation

HRID 1755273 reaction equation
Cl.[C:2]1([N:11]2[CH2:15][CH2:14][C@H:13]([NH2:16])[CH2:12]2)[C:3]2[N:4]([CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:6][N:7]=1.[C:17]1([C:23]2[O:27][N:26]=[C:25]([C:28](O)=[O:29])[N:24]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)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.C(OCC)(=O)C>[C:17]1([C:23]2[O:27][N:26]=[C:25]([C:28]([NH:16][C@H:13]3[CH2:14][CH2:15][N:11]([C:2]4[C:3]5[N:4]([CH:8]=[CH:9][CH:10]=5)[CH:5]=[CH:6][N:7]=4)[CH2:12]3)=[O:29])[N:24]=2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 521913N,N-Diethyl-2-propanamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 218070875-Phenyl-1,2,4-oxadiazole-3-carboxylic acidHCID 86720547(S)-1-(pyrrolo[1,2-a]pyrazin-1-yl)pyrrolidin-3-amine hydrochloride salt

Product 1

HCID 75202694
(S)-5-phenyl-N-(1-(pyrrolo[1,2-a]pyrazin-1-yl)pyrrolidin-3-yl)-1,2,4-oxadiazole-3-carboxamide
Yield 18%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of (S)-1-(pyrrolo[1,2-a]pyrazin-1-yl)pyrrolidin-3-amine hydrochloride salt (90 mg, 0.32 mmol) and 5-phenyl-1,2,4-oxadiazole-3-carboxylic acid (58 mg, 0.3 mmol) in DMF (5 mL) was added diethylisopropyl amine (650 mg, 5 mmol), followed by HATU (120 mg, 0.31 mmol). The resulting solution was stirred at room temperature for 1 h. The reaction mixture was diluted with ethyl acetate and washed with saturated aqueous solutions of KH2PO4 and NaHCO3, followed by brine. The organic layer was concentrated in vacuo and the residue was purified by silica gel flash chromatography (2 to 5% MeOH in CH2Cl2 as eluent) followed by reverse phase HPLC (acetonitrile-H2O with 0.1% TFA as eluent) to give 15 mg of the title compound (18% yield) as white solid. MS: (ES) m/z found 374.1.

Workup

  1. washwashed with saturated aqueous solutions of KH2PO4 and NaHCO3
  2. concentrationThe organic layer was concentrated in vacuo
  3. customthe residue was purified by silica gel flash chromatography (2 to 5% MeOH in CH2Cl2 as eluent)

Sources & evidence

ORD record
ord-3e578cecbebe425983a148eab1884e32
Source dataset
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09169261B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes