Trifluoroacetic acid → HCID 86616581, compound

HRID 907547Notes

Reaction equation

HRID 907547 reaction equation
C([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)=[N:18][C:17]([C:28]#[N:29])=[C:16]([C:30]#[N:31])[N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.[F:39][C:40]([F:55])([F:54])[C:41]1[CH:42]=[C:43]([N:51]=C=O)[CH:44]=[C:45]([C:47]([F:50])([F:49])[F:48])[CH:46]=1>C(Cl)Cl>[F:39][C:40]([F:54])([F:55])[C:41]1[CH:42]=[C:43]([NH:51][C:6]([N:8]2[CH2:9][CH2:10][N:11]([C:14]3[C:19]([O:20][CH2:21][C:22]4[CH:23]=[CH:24][N:25]=[CH:26][CH:27]=4)=[N:18][C:17]([C:28]#[N:29])=[C:16]([C:30]#[N:31])[N:15]=3)[CH2:12][CH2:13]2)=[O:5])[CH:44]=[C:45]([C:47]([F:48])([F:50])[F:49])[CH:46]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 27333143,5-Bis(trifluoromethyl)phenyl isocyanateHCID 67387573HCID 67387573, compound

Product 1

HCID 86616581HCID 86616581, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 5′,6′-Dicyano-3′-(pyridin-4-ylmethoxy)-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid tert-butyl ester (100 mg) and 30% TFA in DCM (11 ml) was stirred for 2 hours. The mixture was concentrated in vacuo to dryness. To the residue was added DCM (5 ml), TEA (0.31 mmol, 51 ul), and 3,5-bis(trifluoromethyl)phenyl isocyanate (0.15 mmol, 26 ul). The resulting mixture was stirred at room temperature for 3 hours. After concentrated in vacuo, the crude product was purified by column on silica using 70% EtOAc/Hexanes to give the product N-[3,5-bis(trifluoromethyl)phenyl]-4-{5,6-dicyano-3-[(pyridin-4-ylmethyl)oxy]pyrazin-2-yl}piperazine-1-carboxamide. 1H NMR (CD3OD) 8.594 (s, 2H), 8.073 (s, 2H), 7.555-7.534 (m, 3H), 5.584 (s, 2H), 4.043-4.029 (m, 4H), 3.739-3.713 (m, 4H) ppm.

Workup

  1. concentrationThe mixture was concentrated in vacuo to dryness
  2. stirringThe resulting mixture was stirred at room temperature for 3 hours
  3. concentrationAfter concentrated in vacuo
  4. customthe crude product was purified by column on silica using 70% EtOAc/Hexanes

Sources & evidence

ORD record
ord-303f6a1f0f3845adba408a2d4783962c
Source dataset
uspto-grants-2011_09
Patent number
US08013156B2

Reaction notes

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