Pyridine → HCID 86585615, compound

HRID 480188

Reaction equation

HRID 480188 reaction equation
[NH2:1][C:2]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:3]=1[O:4][CH2:5][C:6]([N:8]1[CH2:13][C@H:12]([CH3:14])[N:11]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH2:10][C@H:9]1[CH3:23])=[O:7].N1C=CC=CC=1.Cl[C:36]([O:38][C:39]1[CH:44]=[CH:43][C:42]([N+:45]([O-:47])=[O:46])=[CH:41][CH:40]=1)=[O:37]>ClCCl>[N+:45]([C:42]1[CH:41]=[CH:40][C:39]([O:38][C:36](=[O:37])[NH:1][C:2]2[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:3]=2[O:4][CH2:5][C:6]([N:8]2[CH2:13][C@H:12]([CH3:14])[N:11]([CH2:15][C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[CH2:10][C@H:9]2[CH3:23])=[O:7])=[CH:44][CH:43]=1)([O-:47])=[O:46]

Participants

5

Reactant 3

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 540805932-(2-amino-4-chloro-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone

Product 1

HCID 86585615HCID 86585615, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2R, 5S)-2-(2-amino-4-chloro-phenoxy)-1-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-ethanone (0.150 g, 0.37 mmol) in dichloromethane (7 ml) was added pyridine (0.066 ml, 0.82 mmol) followed by 4-nitrophenyl chloroformate (0.075 g, 0.41 mmol). The reaction was stirred at ambient temperature for 3½ hours. The reaction mixture was concentrated followed by chromatography on silica gel to give the title compound (0.153 g, 74% yield).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-9e0a54cf26644a20845e0a5ab1005076
Source dataset
uspto-grants-2003_11
Patent number
US06649611B2

Linked notes

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