2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → HCID 86729578, compound

HRID 2175426Notes

Reaction equation

HRID 2175426 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCOC1N(C(OCC)=O)C2C(=CC=CC=2)C=C1.[C:31]([NH:37][NH2:38])(=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33]>C(Cl)Cl>[O:12]=[C:10]([NH:38][NH:37][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 5451472,2-Dimethylpropanehydrazide

Product 1

HCID 86729578HCID 86729578, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(tert-butoxycarbonylamino)acetic acid (200 mg, 1.14 mmol) and EEDQ (282 mg, 1.26 mmol) in DCM (5 mL) was stirred at room temperature for 15 min, then pivalohydrazide (145 mg, 1.26 mmol) was added and the mixture was continued stirring overnight. The reaction mixture was concentrated and purified by reverse phase chromatography to afford the title compound (100 mg, 32%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.98 (s, 1H), 8.28 (s, 1H), 5.24 (s, 1H), 3.92 (d, J=5.8 Hz, 2H), 1.46 (s, 9H), 1.26 (s, 9H); LRMS (ES) calculated M+Na for C21H25N5O4: 296.2. Found: 296.0.

Workup

  1. stirringthe mixture was continued stirring overnight
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by reverse phase chromatography

Sources & evidence

ORD record
ord-4088e71f1f94413aa7ce1de8b1544c7a
Source dataset
uspto-grants-2015_06
Patent number
US09062059B2

Reaction notes

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