Pyrrolidine → HCID 53834865, compound

HRID 1858088Notes

Reaction equation

HRID 1858088 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:30])=[C:24]([C:27]([OH:29])=O)[CH:25]=2)[NH:20][C:19](=[O:31])[C:18]=1[C:32]1[CH:37]=[C:36]([CH3:38])[CH:35]=[C:34]([CH3:39])[CH:33]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.CN(C)[CH2:43][CH2:44][CH2:45][N:46]=[C:47]=NCC.ON1C2C=CC=CC=2N=N1.N1CCCC1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:30])=[C:24]([C:27]([N:46]3[CH2:47][CH2:43][CH2:44][CH2:45]3)=[O:29])[CH:25]=2)[NH:20][C:19](=[O:31])[C:18]=1[C:32]1[CH:37]=[C:36]([CH3:38])[CH:35]=[C:34]([CH3:39])[CH:33]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 4

HCID 31268PyrrolidineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22124479HCID 22124479, compound

Product 1

HCID 53834865HCID 53834865, compoundYield 48.7%

Procedure

To a solution of 4-[2-(1-tert-butoxycarbonyl-piperidin-2-yl)-ethoxy]-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydro-quinoline-6-carboxylic acid (15 mg in 0.6 mL of dry methylene chloride) was added 8.0 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) followed by 6.0 mg 1-hydroxybenzotriazole (HOBt) and the mixture stirred for 10 minutes. At this time, 9.4 mg of pyrrolidine and the reaction allowed to proceed at room temperature. After 4 hours, the mixture was concentrated in vacuo and purified by flash chromatography on silica gel (methylene chloride:10% ammonium hydroxide in methanol, 95:5) to give the tilte compound (8 mg).

Workup

  1. customto proceed at room temperature
  2. waitAfter 4 hours
  3. concentrationthe mixture was concentrated in vacuo
  4. custompurified by flash chromatography on silica gel (methylene chloride:10% ammonium hydroxide in methanol, 95:5)

Sources & evidence

ORD record
ord-6de998d17a7c47fda93e1c65cdfd9127
Source dataset
uspto-grants-2000_11
Patent number
US06150352

Reaction notes

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