1,2-Dichloroethane → HCID 68297359, compound

HRID 919848Notes

Reaction equation

HRID 919848 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[C:13]([OH:21])[C:14]([C:18]([OH:20])=O)=[N:15][CH:16]=2)[CH:11]=[C:10]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:9]1=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.Cl.[CH2:44]([O:46][C:47](=[O:52])[CH2:48][CH2:49][CH2:50][NH2:51])[CH3:45].CCN(C(C)C)C(C)C>CCOC(C)=O.C(Cl)Cl>[CH2:44]([O:46][C:47](=[O:52])[CH2:48][CH2:49][CH2:50][NH:51][C:18]([C:14]1[C:13]([OH:21])=[C:12]2[C:17](=[CH:16][N:15]=1)[N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9](=[O:28])[C:10]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[CH:11]2)=[O:20])[CH3:45]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 126496614-Aminobutyrate ethyl hydrochlorideHCID 68297349HCID 68297349, compound

Product 1

HCID 68297359HCID 68297359, compoundYield 28.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Benzyl-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid (35 mg, 0.094 mmol) and HOBt (13 mg, 0.094 mmol) were added to 2 mL of CH2Cl2. EDC (25 mg, 0.13 mmol) was added, and the mixture was stirred for 10 min. 4-Amino-butyric acid ethyl ester HCl salt (16 mg, 0.094 mmol) and Hunig's base (0.033 mL, 0.19 mmol) were then added, and the mixture was stirred for 16 h. The mixture was diluted with EtOAc (40 mL) and washed with 0.1 M HCl and brine. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by silica gel chromatography (0-40% EtOAc/hexanes+2% AcOH) to give 13 mg of the title compound. MS: (+) m/z 486.39 (M+1).

Workup

  1. stirringthe mixture was stirred for 16 h
  2. washwashed with 0.1 M HCl and brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by silica gel chromatography (0-40% EtOAc/hexanes+2% AcOH)

Sources & evidence

ORD record
ord-6de7871d0f434ac39f7f6ce7efc26859
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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