HCID 57467433, compound → HCID 178458317, compound

HRID 1890801Notes

Reaction equation

HRID 1890801 reaction equation
[C:1]([N:3]=[C:4](OCC)[C:5]([CH3:14])([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:6])#[N:2].[NH2:18][C:19]12[CH2:25][C:22]([C:26]([NH2:28])=[O:27])([CH2:23][CH2:24]1)[CH2:21][CH2:20]2>C(O)C.CN(C)C1C=CN=CC=1>[C:1]([N:3]=[C:4]([NH:18][C:19]12[CH2:25][C:22]([C:26]([NH2:28])=[O:27])([CH2:21][CH2:20]1)[CH2:23][CH2:24]2)[C:5]([CH3:6])([O:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH3:14])#[N:2]

Participants

5

Reactant 2

HCID 57467433HCID 57467433, compoundHCID 86646771HCID 86646771, compound

Product 1

HCID 178458317HCID 178458317, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 702EthanolSolvent

Procedure

To a mixture of ethyl N-cyano-2-methyl-2-phenoxypropanimidoate (CI-1) (300 mg, 1.29 mmol) and 4-aminobicyclo[2.2.1]heptane-1-carboxamide (BA-7) (217 mg, 1.29 mmol) in ethanol (3 mL) was added 4-(dimethylamino)pyridine (47 mg, 0.387 mmol). The mixture was stirred at room temperature for 5 hours and then heated to 75° C. and stirred overnight. After concentration, the residue was purified by preparative reverse phase HPLC [Waters 2767; Benetnach 10-C18 20×250 mm, 10 μm; 35-85% acetonitrile/water (0.05% trifluoroacetic acid), 30 mL/minute; detection at 214 and 254 nm] to give the titled compound. 1H NMR (400 MHz, CD3OD) δ ppm 7.34 (t, J=7.8 Hz, 2H), 7.14 (t, J=7.4 Hz, 1H), 7.0 (d, J=8.4 Hz, 2H), 2.10-2.15 (m, 4H), 2.01-2.03 (m, 4H), 1.79-1.83 (m, 2H), 1.72 (s, 6H); LCMS (ESI+) m/z 341.7 (M+H)+.

Workup

  1. temperatureheated to 75° C.
  2. stirringstirred overnight
  3. concentrationAfter concentration
  4. customthe residue was purified by preparative reverse phase HPLC [Waters 2767; Benetnach 10-C18 20×250 mm, 10 μm; 35-85% acetonitrile/water (0.05% trifluoroacetic acid), 30 mL/minute; detection at 214 and 254 nm]

Sources & evidence

ORD record
ord-1a8fe3a3d8dc464489e27f04b1631f4b
Source dataset
uspto-grants-2013_08
Patent number
US08507493B2

Reaction notes

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