1,2-Dichloroethane → HCID 68457914, compound

HRID 474199Notes

Reaction equation

HRID 474199 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:10]([OH:12])=O)=[N:6][C:7]=1[C:8]#[N:9].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[CH:27]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)([CH3:29])[CH3:28]>CN(C=O)C.C(Cl)Cl>[Br:1][C:2]1[C:7]([C:8]#[N:9])=[N:6][C:5]([C:10]([N:33]2[CH2:34][CH2:35][N:30]([CH:27]([CH3:29])[CH3:28])[CH2:31][CH2:32]2)=[O:12])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 780131-IsopropylpiperazineHCID 574252995-Bromo-6-cyanopyridine-2-carboxylic acid

Product 1

HCID 68457914HCID 68457914, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-bromo-6-cyano-pyridine-2-carboxylic acid (875 mg, 3.85 mmol), HOBt (882 mg, 6.53 mmol), and EDC (1.11 g, 5.80 mmol) in DMF (32 mL) was stirred for 5 min and then treated with 1-isopropyl-piperazine (943 mg, 7.35 mmol). After 5 h, the mixture was diluted with DCM, washed with 1 N NaOH and water, dried, and concentrated. Purification of the residue by FCC gave a viscous foam that crystallized upon standing. Further purification by reverse-phase HPLC gave the title compound (476 mg, 37%). MS (ESI): mass calcd. for C14H17BrN4O, 336.06; m/z found, 337.2 [M+H]+. 1H NMR (d6-acetone): 8.43 (d, J=8.4 Hz, 1H), 7.83 (d, J=8.4 Hz, 1H), 3.70-3.68 (m, 2H), 3.51-3.49 (m, 2H), 2.73 (septet, J=6.6 Hz, 1H), 2.58-2.56 (m, 2H), 2.50-2.48 (m, 2H), 1.01 (d, J=6.6 Hz, 6H).

Workup

  1. waitAfter 5 h
  2. washwashed with 1 N NaOH and water
  3. customdried
  4. concentrationconcentrated
  5. customPurification of the residue by FCC
  6. customgave a viscous foam that
  7. customcrystallized
  8. customFurther purification by reverse-phase HPLC

Sources & evidence

ORD record
ord-be17323774b740f1be66f48e45c3e7d5
Source dataset
uspto-grants-2014_01
Patent number
US08637520B2

Reaction notes

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