1,2-Dichloroethane → HCID 10174641, compound

HRID 1392126Notes

Reaction equation

HRID 1392126 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][C:11]([C:21]([OH:23])=O)=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.[NH2:24][N:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.C(Cl)CCl>CN(C1C=CN=CC=1)C>[N:25]1([NH:24][C:21]([C:11]2[CH:10]=[N:9][C:8]([C:5]3[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=3)=[C:13]([C:14]3[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=3)[N:12]=2)=[O:23])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 166581-AminopiperidineHCID 69051372HCID 69051372, compound

Product 1

HCID 10174641HCID 10174641, compoundYield 5.4%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Conditions

Temperature
25 °C

Procedure

To 5,6-Bis-(4-bromophenyl)-pyrazine-2-carboxylic acid (108 mg, 0.25 mmol) from Preparation A, step (b), DMAP (0.025 mmol, in 500 μl DCM), 1-aminopiperidine (0.25 mmol, in 1100 μl DCM), EDC (0.27 mmol, in 1100 μl DCM and cooled to 8° C.) were added. The reaction mixture was stirred at 25° C. for 20 h, then washed with saturated NaHCO3 solution, dried (MgSO4), filtered and evaporated. Semipreparatory HPLC (0.01% TEA in the buffered phase) gave the subtitle compound (6.7 mg, 5.4%).

Workup

  1. additionwere added
  2. washwashed with saturated NaHCO3 solution
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-34cc4585bdd249d089be8b6884055c14
Source dataset
uspto-grants-2008_03
Patent number
US07342019B2

Reaction notes

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