1-Aminopiperidine → N-(piperidin-1-yl)-4-{4-[3-(1H-pyrazol-4-yl)pyrrolidine-1-carbonyl]-3,4-dihydro-2H-quinoxalin-1-yl}benzamide

HRID 551820Notes

Reaction equation

HRID 551820 reaction equation
[NH:1]1[CH:5]=[C:4]([CH:6]2[CH2:10][CH2:9][N:8]([C:11]([N:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]([C:23]4[CH:31]=[CH:30][C:26]([C:27]([OH:29])=O)=[CH:25][CH:24]=4)[CH2:15][CH2:14]3)=[O:12])[CH2:7]2)[CH:3]=[N:2]1.[NH2:32][N:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1.OC1C2N=NNC=2C=CC=1.CCN=C=NCCCN(C)C.Cl>O1CCOCC1.CN(C)C=O>[N:33]1([NH:32][C:27](=[O:29])[C:26]2[CH:30]=[CH:31][C:23]([N:16]3[C:17]4[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=4)[N:13]([C:11]([N:8]4[CH2:9][CH2:10][CH:6]([C:4]5[CH:3]=[N:2][NH:1][CH:5]=5)[CH2:7]4)=[O:12])[CH2:14][CH2:15]3)=[CH:24][CH:25]=2)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

6

Reactant 4

HCID 166581-AminopiperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67189619HCID 67189619, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 24853022N-(piperidin-1-yl)-4-{4-[3-(1H-pyrazol-4-yl)pyrrolidine-1-carbonyl]-3,4-dihydro-2H-quinoxalin-1-yl}benzamideYield 58.5%

Reagents, catalysts & solvents 1

HCID 217120691,4-dioxane N,N-dimethylformamideSolvent

Procedure

0.4 g of 4-[4-{[3-(1H-pyrazol-4-yl)pyrrolidin-1-yl]carbonyl}-3,4-dihydroquinoxalin-1(2H)-yl]benzoic acid, 0.19 g of 1-aminopiperidine, 0.26 g of hydroxybenzotriazole, 0.37 g of EDC.HCl and 7 ml of a dioxane/dimethylformamide 5/2 mixture are introduced into a 100 ml round-bottomed flask equipped with a magnetic stirrer. The reaction mixture is stirred at ambient temperature for 20 h and concentrated under vacuum. The residue is chromatographed on silica gel eluted with a dichloromethane/acetone/methanol/NH4OH 88/10/2/0.2 and then 82/15/3/0.3 mixture. After triturating in ethyl ether, 0.28 g of N-(piperidin-1-yl)-4-{4-[3-(1H-pyrazol-4-yl)pyrrolidine-1-carbonyl]-3,4-dihydro-2H-quinoxalin-1-yl}benzamide is obtained.

Workup

  1. customequipped with a magnetic stirrer
  2. concentrationconcentrated under vacuum
  3. customThe residue is chromatographed on silica gel
  4. washeluted with a dichloromethane/acetone/methanol/NH4OH 88/10/2/0.2
  5. customAfter triturating in ethyl ether

Sources & evidence

ORD record
ord-48bce55cd430466fabdbd8a0c373acb1
Source dataset
uspto-grants-2011_05
Patent number
US07947834B2

Reaction notes

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