Dichloromethane → HCID 11756624, compound

HRID 907531Notes

Reaction equation

HRID 907531 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]2[C:10]([N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)=[N:11][CH:12]=[CH:13][N:14]=2)=[CH:3][CH:2]=1.C(Cl)Cl.C(N(CC)CC)C.[N:31]([C:34]1[CH:39]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:37]=[C:36]([C:44]([F:47])([F:46])[F:45])[CH:35]=1)=[C:32]=[O:33]>CCOC(C)=O>[F:41][C:40]([F:42])([F:43])[C:38]1[CH:39]=[C:34]([NH:31][C:32]([N:18]2[CH2:19][CH2:20][N:15]([C:10]3[C:9]([O:8][CH2:7][C:4]4[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=4)=[N:14][CH:13]=[CH:12][N:11]=3)[CH2:16][CH2:17]2)=[O:33])[CH:35]=[C:36]([C:44]([F:47])([F:45])[F:46])[CH:37]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 27333143,5-Bis(trifluoromethyl)phenyl isocyanateHCID 59013957HCID 59013957, compound

Product 1

HCID 11756624HCID 11756624, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a round bottom flask equipped with a magnetic stir bar was added 3′-(pyridin-4-ylmethoxy)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (0.3 g, 0.97 mmol, 1.0 eq.), dry CH2Cl2 (3 mL), triethyl amine (TEA) (0.54 g, 0.4 mL, 5.1 mmol, 5 eq) and was then cooled in an ice bath. 1-Isocyanato-3,5-bis-trifluoromethyl-benzene (0.29 g, 0.2 ml, 1.2 mmol, 1.2 eq.) was then added drop wise to the reaction mixture. Total reaction time was 3 hours at which point the reaction was diluted with 3× the volume EtOAc. This solution was then washed 3× with NaHCO3 and 2× with brine. The organic layer was dried with Na2SO4, concentrated, and the solid was columned with a Biotage system using a gradient. The initial eluent was 1:1 ethyl acetate/hexane followed by an eluent 3:1 ethyl acetate/hexane. The solvent was then removed and dried under high vacuum to yield the title compound (0.16 g, 32% yield) as a solid. 1H NMR (CDCl3) 8.63 (d, 2H), 7.90 (s, 2H), 7.81 (d, 1H), 7.62 (d, 1H), 7.54 (s, 1H), 7.34 (d, 2H), 7.26 (s, 2H), 6.78 (s, 1H), 5.48 (s, 2H), 3.67 (m, 8H) ppm.

Workup

  1. customTo a round bottom flask equipped with a magnetic stir bar
  2. temperaturewas then cooled in an ice bath
  3. washThis solution was then washed 3× with NaHCO3 and 2× with brine
  4. dry with materialThe organic layer was dried with Na2SO4
  5. concentrationconcentrated
  6. customThe solvent was then removed
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-6cd7977ce5524f76a37f508ce9ee9a3d
Source dataset
uspto-grants-2011_09
Patent number
US08013156B2

Reaction notes

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