1,2-Dichloroethane → tert-butyl 4-(2-chloroisonicotinoyl)tetrahydro-1(2H)-pyrazinecarboxylate

HRID 1355543Notes

Reaction equation

HRID 1355543 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([NH:7][CH3:8])=[O:6].[C:12]([O:16][C:17]([N:19]1[CH2:24]CN[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([N:7]1[CH2:21][CH2:20][N:19]([C:17]([O:16][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:18])[CH2:24][CH2:8]1)=[O:6]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 143452tert-Butyl piperazine-1-carboxylateHCID 151158492-chloro-N-methylisonicotinamide

Product 1

HCID 2774091tert-butyl 4-(2-chloroisonicotinoyl)tetrahydro-1(2H)-pyrazinecarboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-Chloroisonicotinic acid (12-2, 250 mg, 1.59 mmole), tert-butylpiperazine-1-carboxylate (355 mg, 1.9 mmole), EDC (365 mg, 1.9 mmole), and HOBt (257 mg, 1.9 mmole) were combined in dry DMF (10 mL). To this was added Et3N (0.55 mL, 3.97 mmole) at RT. After 18 hr the mixture was diluted with H2O and extracted with EtOAc (4×). The combined organic layers were washed with H2O, brine; then dried (MgSO4), filtered, and concentrated to give the titled compound as an amber oil which was used immediately in the next step.

Workup

  1. extractionextracted with EtOAc (4×)
  2. washThe combined organic layers were washed with H2O, brine
  3. dry with materialthen dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-154a464909d94bd0b59cce6dd717f1d6
Source dataset
uspto-grants-2003_07
Patent number
US06586424B2

Reaction notes

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