Chlorosuccinimide → 1,1-dimethylethyl (2S)-2-[(3-chloro-7-methylimidazo[1,2-a]pyrimidin-2-yl)methyl]-1-piperidinecarboxylate

HRID 418042Notes

Reaction equation

HRID 418042 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]2[CH:8]=[C:9]([CH2:11][C@@H:12]3[CH2:17][CH2:16][CH2:15][CH2:14][N:13]3[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[N:10]=[C:4]2[N:3]=1.C1C(=O)N([Cl:32])C(=O)C1>C(Cl)Cl>[Cl:32][C:8]1[N:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[N:3][C:4]2=[N:10][C:9]=1[CH2:11][C@@H:12]1[CH2:17][CH2:16][CH2:15][CH2:14][N:13]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 593766971,1-dimethylethyl (2S)-2-[(7-methylimidazo[1,2-a]pyrimidin-2-yl)methyl]-1-piperidinecarboxylate

Product 1

HCID 593767001,1-dimethylethyl (2S)-2-[(3-chloro-7-methylimidazo[1,2-a]pyrimidin-2-yl)methyl]-1-piperidinecarboxylateYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl (2S)-2-[(7-methylimidazo[1,2-a]pyrimidin-2-yl)methyl]-1-piperidinecarboxylate (0.350 g, 0.53 mmol) in DCM (5 ml) was added NCS (0.071 g, 0.53 mmol) and the reaction mixture was stirred for 1.5 h at rt. The solvent was evaporated and the residue purified by cromatography on silica gel (Biotage, NH phase 25+M, Cy/EtOAc from 100/0 to 50/50). Collected fractions gave the title compound (0.085 g, 0.23 mmol, 44% yield) as a colourless solid. UPLC: rt=0.70, peak observed: 365 (M+1, 100%) and 367 (M+1, 33%). C18H25ClN4O2 requires 365.

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by cromatography on silica gel (Biotage, NH phase 25+M, Cy/EtOAc from 100/0 to 50/50)

Sources & evidence

ORD record
ord-a765a43e58bf490fa9e32e6dfafe6492
Source dataset
uspto-grants-2012_01
Patent number
US08093255B2

Reaction notes

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