3,4,5-Trichloropyridazine → 4-[(5,6-Dichloro-pyridazin-4-ylamino)-methyl]-piperidine-1-carboxylic acid benzyl ester

HRID 1827161Notes

Reaction equation

HRID 1827161 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][CH:5]=[C:6](Cl)[C:7]=1[Cl:8].CCN(C(C)C)C(C)C.[NH2:19][CH2:20][CH:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:28])[CH2:23][CH2:22]1>CC(O)C>[CH2:30]([O:29][C:27]([N:24]1[CH2:25][CH2:26][CH:21]([CH2:20][NH:19][C:6]2[C:7]([Cl:8])=[C:2]([Cl:1])[N:3]=[N:4][CH:5]=2)[CH2:22][CH2:23]1)=[O:28])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 701113,4,5-TrichloropyridazineHCID 81531DiisopropylethylamineHCID 219554994-Aminomethyl-1-N-Cbz-piperidine

Product 1

HCID 101352914-[(5,6-Dichloro-pyridazin-4-ylamino)-methyl]-piperidine-1-carboxylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a stirred solution of 3,4,5-trichloropyridazine (2.22 g, 12.08 mmol) and DIPEA (4.21 mL, 24.16 mmol) in IPA (25 mL) was added benzyl-4-(aminomethyl)piperidine-1-carboxylate (EXAMPLE 13, Step 1, 3.00 g, 12.08 mmol). The resulting reaction solution was stirred at rt for 5 h, then concentrated in vacuo. The residue was dissolved in CH2Cl2 (200 mL), washed with water (50 mL), dried over Na2SO4, filtered and concentrated. The crude product was purified by silica gel chromatography (1-7 (10% NH4OH in MeOH)/99-93 CH2Cl2) to give 4-[(5,6-dichloro-pyridazin-4-ylamino)-methyl]-piperidine-1-carboxylic acid benzyl ester. M.S.(M+1):395.28

Workup

  1. customThe resulting reaction solution
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in CH2Cl2 (200 mL)
  4. washwashed with water (50 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by silica gel chromatography (1-7 (10% NH4OH in MeOH)/99-93 CH2Cl2)

Sources & evidence

ORD record
ord-ea04b501e9d14789815c27a8136fa85f
Source dataset
uspto-grants-2006_05
Patent number
US07053089B2

Reaction notes

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