4-[(Pyridazin-4-ylamino)-methyl]-piperidine → 4-[(Pyridazin-4-ylamino)-methyl]-piperidine-1-carboxylic acid-4-fluoro-benzyl ester

HRID 1351527Notes

Reaction equation

HRID 1351527 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][CH2:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:3][N:2]=1.O=C1CCC(=O)N1[O:22][C:23](=O)[O:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1>CN(C=O)C>[F:32][C:29]1[CH:28]=[CH:27][C:26]([CH2:25][O:24][C:23]([N:12]2[CH2:11][CH2:10][CH:9]([CH2:8][NH:7][C:4]3[CH:5]=[CH:6][N:1]=[N:2][CH:3]=3)[CH2:14][CH2:13]2)=[O:22])=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 221355874-[(Pyridazin-4-ylamino)-methyl]-piperidineHCID 857843262,5-Dioxo-1-pyrrolidinyl (4-fluorophenyl)methyl carbonate

Product 1

HCID 101545434-[(Pyridazin-4-ylamino)-methyl]-piperidine-1-carboxylic acid-4-fluoro-benzyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-[(pyridazin-4-ylamino)-methyl]-piperidine (0.20 g, 1.04 mmol, from EXAMPLE 66, Step 1) in DMF (3 mL) was added carbonic acid-4-fluoro-benzyl ester 2,5-dioxo-pyrrolidin-1-yl ester (0.28 g, 1.04 mmol). The resulting reaction solution was stirred at rt for 0.5 h, then concentrated in vacuo. The residue was purified by silica gel chromatography (1–7 (10% NH4OH in MeOH)/99–93 CH2Cl2) to give 4-[(pyridazin-4-ylamino)-methyl]-piperidine-1-carboxylic acid-4-fluoro-benzyl ester. M.S. (M+1): 345.29

Workup

  1. customThe resulting reaction solution
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by silica gel chromatography (1–7 (10% NH4OH in MeOH)/99–93 CH2Cl2)

Sources & evidence

ORD record
ord-fae56ceed6344ccc91d9c6e5bbde8ec5
Source dataset
uspto-grants-2007_05
Patent number
US07217716B2

Reaction notes

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