Pyridine → HCID 11705140, compound

HRID 1091255Notes

Reaction equation

HRID 1091255 reaction equation
Cl[C:2](OC1C=CC([N+]([O-])=O)=CC=1)=[O:3].[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][N:16]=1.N1C=CC=CC=1.[Cl-].[OH:29][C@H:30]1[CH2:34][NH2+:33][C@@H:32]([C:35](=[O:50])[NH:36][C:37]2[CH:42]=[CH:41][C:40]([N:43]3[CH:48]=[CH:47][CH:46]=[CH:45][C:44]3=[O:49])=[CH:39][CH:38]=2)[CH2:31]1.C(N(C(C)C)C(C)C)C>ClCCl>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([NH:14][C:2]([N:33]2[CH2:34][C@H:30]([OH:29])[CH2:31][C@@H:32]2[C:35]([NH:36][C:37]2[CH:38]=[CH:39][C:40]([N:43]3[CH:48]=[CH:47][CH:46]=[CH:45][C:44]3=[O:49])=[CH:41][CH:42]=2)=[O:50])=[O:3])=[N:16][CH:17]=1

Participants

7

Reactant 5

HCID 1049PyridineHCID 661742-Amino-5-chloropyridineHCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 57463486HCID 57463486, compound

Product 1

HCID 11705140HCID 11705140, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

894 mg (4.43 mmol) of 4-nitrophenyl chloroformate are added to a solution of 570 mg (4.43 mmol) of 2-amino-5-chloropyridine and 0.73 ml (9.0 mmol) of pyridine in 50 ml of dichloromethane, and the mixture is stirred at room temperature for 1 hour. 1.49 g (4.43 mmol) of (2R,4R)-4-hydroxy-2-[4-(2-oxo-2H-pyridin-1-yl)phenylcarbamoyl]pyrrolidinium chloride and 1.5 ml (9.0 mmol) of N-ethyldiisopropylamine are added to the resultant suspension, and the reaction mixture is stirred at room temperature for 18 hours. The reaction mixture is evaporated, and the residue is chromatographed on a silica-gel column with dichloromethane/methanol 95:5 as eluent, giving 1-N-[(5-chloropyridin-2-yl)]-2-N-{[4-(2-oxo-2H-pyridin-1-yl)phenyl]}-(2R,4R)-4-hydroxypyrrolidine-1,2-dicarboxamide (“A6”) as a colourless solid, ESI 454.

Workup

  1. stirringthe reaction mixture is stirred at room temperature for 18 hours
  2. customThe reaction mixture is evaporated
  3. customthe residue is chromatographed on a silica-gel column with dichloromethane/methanol 95:5 as eluent

Sources & evidence

ORD record
ord-94fbd57d5b7b4093b218273f22043dcf
Source dataset
uspto-grants-2012_03
Patent number
US08129373B2

Reaction notes

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