Diisopropylethylamine → HCID 24968342, compound

HRID 1666338Notes

Reaction equation

HRID 1666338 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][C:5](=[CH:8][C:9]2[CH:10]=[C:11]([CH:23]=[CH:24][CH:25]=2)[O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][N:14]=2)[CH2:4][CH2:3]1.[CH3:26][O:27][C:28]1[N:29]=[CH:30][C:31]([NH:34][C:35](=O)[O:36]C2C=CC=CC=2)=[N:32][CH:33]=1.NC1C=NC(OC)=CN=1.C(N(C(C)C)CC)(C)C>CS(C)=O>[CH3:26][O:27][C:28]1[N:29]=[CH:30][C:31]([NH:34][C:35]([N:2]2[CH2:7][CH2:6][C:5](=[CH:8][C:9]3[CH:25]=[CH:24][CH:23]=[C:11]([O:12][C:13]4[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:20])[F:21])=[CH:15][N:14]=4)[CH:10]=3)[CH2:4][CH2:3]2)=[O:36])=[N:32][CH:33]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 145364295-Methoxypyrazin-2-amineHCID 66876115HCID 66876115, compoundHCID 668761612-(3-(Piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridine hydrochloride

Product 1

HCID 24968342HCID 24968342, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 2-(3-piperidin-4-ylidenemethyl-phenoxy)-5-trifluoromethyl-pyridine hydrochloride (0.371 g, 1.00 mmol) (from Example 1, Step 5) and phenyl 5-methoxypyrazin-2-ylcarbamate (0.254 g, 1.2 mmol, prepared according to the procedure described in Synthesis, 1997, 1189-1194 from 2-amino-5-methoxypyrazine) in DMSO (2.5 mL) was treated with diisopropylethylamine (0.155 g, 1.2 mmol) and was heated to 60° C. After 4 h, the reaction mixture was partitioned between water and ethyl acetate. The organic layer was separated and the aqueous layer was extracted again with ethyl acetate. The combined organic layer was washed with brine and dried over sodium sulfate, filtered and concentrated to a white solid. Trituration with diethyl ether provided the title compound as a white solid (365 mg, 75%). MS (APCI 10V) AP+ 486.25; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.32 (t, J=5.46 Hz, 2H) 2.44 (t, J=5.46 Hz, 2H) 3.47 (t, J=5.46 Hz, 2H) 3.54 (t, J=5.46 Hz, 2H) 3.83 (s, 3H) 6.37 (s, 1H) 7.02-7.05 (m, 2H) 7.11 (d, J=7.8 Hz, 1H) 7.21 (d, J=8.57 Hz, 1H) 7.39 (dt, J=7.6 Hz, 2 Hz, 1H) 7.99 (d, J=1.6 Hz, 1H) 8.21 (dd, J=9.2 Hz, 2.7 Hz, 1H) 8.53 (m, 2H) 9.18 (s, 1H).

Workup

  1. customthe reaction mixture was partitioned between water and ethyl acetate
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted again with ethyl acetate
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to a white solid

Sources & evidence

ORD record
ord-2e6c54e2c5ad486587076df1ada36f2c
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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