Carbonate Ion → HCID 57756826, compound

HRID 227999Notes

Reaction equation

HRID 227999 reaction equation
[C:1]([C:4]12[CH2:11][CH2:10][C:7]([NH:12][CH2:13][C:14]([N:16]3[CH2:20][C@@H:19]([F:21])[CH2:18][C@H:17]3[C:22]#[N:23])=[O:15])([CH2:8][CH2:9]1)[CH2:6][CH2:5]2)([OH:3])=O.ON1C2C=CC=CC=2N=N1.N=C=N.[Cl:37][C:38]1[CH:45]=[CH:44][C:41]([CH2:42][NH2:43])=[CH:40][CH:39]=1.C(=O)([O-])[O-]>ClCCl>[Cl:37][C:38]1[CH:45]=[CH:44][C:41]([CH2:42][NH:43][C:1]([C:4]23[CH2:9][CH2:8][C:7]([NH:12][CH2:13][C:14]([N:16]4[CH2:20][C@@H:19]([F:21])[CH2:18][C@H:17]4[C:22]#[N:23])=[O:15])([CH2:6][CH2:5]2)[CH2:10][CH2:11]3)=[O:3])=[CH:40][CH:39]=1

Participants

7

Reactant 5

HCID 19660Carbonate IonHCID 660364-ChlorobenzylamineHCID 757711-HydroxybenzotriazoleHCID 160435CarbodiimideHCID 57634365(2S,4S)-1-[[N-(4-carboxybicyclo[2,2,2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile

Product 1

HCID 57756826HCID 57756826, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2S,4S)-1-[[N-(4-Carboxybicyclo[2.2.2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (50.0 mg), 1-hydroxybenzotriazole (28.0 mg), PS-carbodiimide (240 mg) and dichloromethane (4 mL) were mixed together and the mixture was stirred at room temperature for 15 minutes. 4-chlorobenzylamine (19.0 μL) was then added and the mixture was stirred at room temperature for further 24 hours. Subsequently, MP-carbonate (270 mg) was added and the mixture was stirred at room temperature for 5 hours and was left overnight. The insoluble material in the mixture was filtered and the filtrate was concentrated under reduced pressure. The resulting residue was then purified by a silica gel column (eluant:dichloromethane:methanol=10:1) to give (2S,4S)-1-[[N-[4-[N-(4-chlorophenylmethyl)amino]carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (29.1 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for further 24 hours
  2. stirringthe mixture was stirred at room temperature for 5 hours
  3. waitwas left overnight
  4. filtrationThe insoluble material in the mixture was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was then purified by a silica gel column (eluant:dichloromethane:methanol=10:1)

Sources & evidence

ORD record
ord-baff4b3aaf194fd1b4dadad878f98562
Source dataset
uspto-grants-2009_07
Patent number
US07560569B2

Reaction notes

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