Triethylamine → 4-[(5-Fluoro-pyrimidin-2-ylamino)-methyl]-piperidine-1-carboxylic acid-4-methyl-benzyl ester

HRID 1351530Notes

Reaction equation

HRID 1351530 reaction equation
[CH3:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][O:7][C:8]([N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][NH2:17])[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.Cl[C:21]1[N:26]=[CH:25][C:24]([F:27])=[CH:23][N:22]=1.C(N(CC)CC)C>CN(C=O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][O:7][C:8]([N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][NH:17][C:21]3[N:26]=[CH:25][C:24]([F:27])=[CH:23][N:22]=3)[CH2:12][CH2:11]2)=[O:9])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5834662-Chloro-5-fluoropyrimidineHCID 161094174-Methylbenzyl 4-(aminomethyl)1-piperidinecarboxylate2×

Product 1

HCID 102697634-[(5-Fluoro-pyrimidin-2-ylamino)-methyl]-piperidine-1-carboxylic acid-4-methyl-benzyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The solution of (4-methyl-benzyl)-4-(aminomethyl)piperidine-1-carboxylate (INTERMEDIATE 2a) (0.20 g, 0.76 mmol), 2-chloro-5-fluoro-pyrimidine (EXAMPLE 71, Step 1) (0.10 g, 0.76 mmol) and triethylamine (0.21 mL, 1.53 mmol) in DMF (1 mL) was heated at 100° C. for 6 h, then concentrated in vacuo. The residue was purified by silica gel chromatography (10 CH2Cl2: 1–10 IPA: 89–80 hexane) to give 4-[(5-fluoro-pyrimidin-2-ylamino)-methyl]-piperidine-1-carboxylic acid-4-methyl-benzyl ester. M.S. (M+1): 359.33

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by silica gel chromatography (10 CH2Cl2: 1–10 IPA: 89–80 hexane)

Sources & evidence

ORD record
ord-ea7b55f74b48437694eb2d3296727137
Source dataset
uspto-grants-2007_05
Patent number
US07217716B2

Reaction notes

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