2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → (S)-1-(1,1-Dioxo-1lambda6-thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid (5-ethyl-4-phenyl-thiazol-2-yl)-amide

HRID 336198Notes

Reaction equation

HRID 336198 reaction equation
[O:1]=[S:2]1(=[O:19])[CH2:7][CH2:6][N:5]([C:8]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]2[C:16]([OH:18])=O)=[O:9])[CH2:4][CH2:3]1.[NH2:20][C:21]1[S:22][C:23]([CH2:32][CH3:33])=[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:25]=1.C(OC1C=CC2C(=CC=CC=2)N1C(OCC)=O)C>ClCCl>[CH2:32]([C:23]1[S:22][C:21]([NH:20][C:16]([C@@H:11]2[CH2:12][CH2:13][CH2:14][CH2:15][N:10]2[C:8]([N:5]2[CH2:4][CH2:3][S:2](=[O:1])(=[O:19])[CH2:7][CH2:6]2)=[O:9])=[O:18])=[N:25][C:24]=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH3:33]

Participants

5

Reactant 3

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 1475602-Thiazolamine, 5-ethyl-4-phenyl-HCID 58563809(2S)-1-[(1,1-Dioxido-4-thiomorpholinyl)carbonyl]-2-piperidinecarboxylic acid

Product 1

HCID 46873413(S)-1-(1,1-Dioxo-1lambda6-thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid (5-ethyl-4-phenyl-thiazol-2-yl)-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-1-(1,1-Dioxo-1λ6-thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid (92 mg; 0.317 mmol) and 2-amino-5-ethyl-4-phenyl-1,3-thiazole (64.8 mg; 0.317 mmol) in dichloromethane (4 mL) is added 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (79.1 mg; 0.32 mmol). The reaction mixture is left stirring at room temperature for 18 hours. The reaction mixture is directly purified by preparative HPLC provides the title compound, m/z 477 [M+H+].

Workup

  1. waitThe reaction mixture is left
  2. customThe reaction mixture is directly purified by preparative HPLC

Sources & evidence

ORD record
ord-0bc276f75f5949db9988b07030642a86
Source dataset
uspto-grants-2014_11
Patent number
US08889670B2

Reaction notes

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