2-Dimethylaminopyridine → HCID 57271532, compound

HRID 2185776Notes

Reaction equation

HRID 2185776 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[C:11]([OH:13])=O.CN(C1C=CC=CN=1)C.CCN=C=NCCCN(C)C.Cl.[NH2:35][C@H:36]([C@H:44]1[O:48][C:47](=[O:49])[C@H:46]([CH2:50][CH2:51][C:52]([F:55])([CH3:54])[CH3:53])[CH2:45]1)[CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C(Cl)Cl.C(OCC)C>[F:55][C:52]([CH3:54])([CH3:53])[CH2:51][CH2:50][C@H:46]1[C:47](=[O:49])[O:48][C@H:44]([C@@H:36]([NH:35][C:11]([C:2]2[CH:3]=[N:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)=[O:13])[CH2:37][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH2:45]1

Participants

7

Reactant 4

HCID 218852-DimethylaminopyridineHCID 96695Quinoxaline-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69911745HCID 69911745, compound

Product 1

HCID 57271532HCID 57271532, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of quinoxaline carboxylic acid (5.05 g, 29.0 mmol) in methylene chloride (100 mL) was added dimethylaminopyridine (DMAP) (3.55 g, 29.0 mmol) and EDCl (5.55 g, 29.0 mmol). The solution was stirred 10 minutes, then the product from Method D, above, (5.68 g, 19.4 mmol) was added in one portion. The solution was stirred for 12 hours, then diluted with diethyl ether and washed with saturated aqueous brine. The organics were dried over magnesium sulfate, and then filtered and concentrated. The crude product was purified by silica gel chromatography to yield the title compound (5.62 g, 64%).

Workup

  1. stirringThe solution was stirred for 12 hours
  2. washwashed with saturated aqueous brine
  3. dry with materialThe organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-31d92074617b47299472c9c70e5bae4e
Source dataset
uspto-grants-2002_06
Patent number
US06403587B1

Reaction notes

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