Triethylamine → HCID 58654468, compound

HRID 1170532Notes

Reaction equation

HRID 1170532 reaction equation
[N:1]1([C:6]2[N:11]=[C:10]([CH:12]3[CH:16]([C:17]([OH:19])=O)[CH2:15][CH2:14][N:13]3[CH3:20])[CH:9]=[C:8]([CH3:21])[N:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[CH2:47]1[O:58][C:57]2[CH:56]=[CH:55][C:51]([CH2:52][CH2:53][NH2:54])=[CH:50][C:49]=2[O:48]1.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[O:58]1[C:57]2[CH:56]=[CH:55][C:51]([CH2:52][CH2:53][NH:54][C:17]([CH:16]3[CH2:15][CH2:14][N:13]([CH3:20])[CH:12]3[C:10]3[CH:9]=[C:8]([CH3:21])[N:7]=[C:6]([N:1]4[CH:5]=[CH:4][N:3]=[CH:2]4)[N:11]=3)=[O:19])=[CH:50][C:49]=2[O:48][CH2:47]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 74246Phenethylamine, 3,4-methylenedioxy-, hydrochlorideHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58654390HCID 58654390, compound

Product 1

HCID 58654468HCID 58654468, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(2-Imidazol-1-yl-6-methyl-pyrimidin-4-yl)-1-methyl-pyrrolidine-3-carboxylic acid (31.9 mg, 0.111 mmol) was dissolved in DMF (1 mL). Next, the HBTU (64.0 mg, 0.167 mmol) was added. The reaction was stirred at room temperature for 30 minutes prior to addition of 3,4-methylenedioxyphenethyl amine hydrochloride (22.4 mg, 0.111 mmol) and triethylamine (50 μL). The reaction was stirred at rt for 12 h then heated to 60° C. for 16 h. After this period, the reaction mixture was transferred to a separatory funnel with ethyl acetate (20 mL). The organic layer was washed with sat. NaHCO3 (aq) (30 mL) and H2O (30 mL). The aqueous layers were back extracted with ethyl acetate (25 mL) and all of the organic portions were combined, dried over Na2SO4 and concentrated down under vacuum. The material was purified by Flash Chromatography (10 g, 0-10% methanol/DCM gradient) to afford 2-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)-1-methyl-pyrrolidine-3-carboxylic acid (2-benzo[1,3]dioxol-5-yl-ethyl)-amide. Product isolated as a mixture of diasteromers; [M+H]+ 435.63.

Workup

  1. stirringThe reaction was stirred at rt for 12 h
  2. temperaturethen heated to 60° C. for 16 h
  3. waitAfter this period
  4. washThe organic layer was washed with sat. NaHCO3 (aq) (30 mL) and H2O (30 mL)
  5. extractionThe aqueous layers were back extracted with ethyl acetate (25 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated down under vacuum
  8. customThe material was purified by Flash Chromatography (10 g, 0-10% methanol/DCM gradient)

Sources & evidence

ORD record
ord-b7e94702c84b4edf81ff0d5c8cb82425
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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