2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → HCID 59452288, compound

HRID 2174715Notes

Reaction equation

HRID 2174715 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][C:10]([CH2:17][O:18][CH3:19])([CH2:14][O:15][CH3:16])[C:11]([OH:13])=O)=[O:8])=[CH:4][CH:3]=1.C(OC1C=CC2C(=CC=CC=2)N1C(OCC)=O)C.[CH3:38][N:39]1[CH2:45][CH2:44][C:43]2[CH:46]=[C:47]([NH2:50])[CH:48]=[CH:49][C:42]=2[CH2:41][CH2:40]1>C1COCC1>[CH3:16][O:15][CH2:14][C:10]([NH:9][C:7]([C:5]1[S:6][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:8])([CH2:17][O:18][CH3:19])[C:11](=[O:13])[NH:50][C:47]1[CH:48]=[CH:49][C:42]2[CH2:41][CH2:40][N:39]([CH3:38])[CH2:45][CH2:44][C:43]=2[CH:46]=1

Participants

5

Reactant 3

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 21822925HCID 21822925, compoundHCID 67456065N-(5-Chlorothiophene-2-carbonyl)-2-(methoxymethyl)-O-methylserine

Product 1

HCID 59452288HCID 59452288, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

0.05 g (0.16 mmol) 2-[(5-chloro-thiophene-2-carbonyl)-amino]-3-methoxy-2-methoxymethyl-propionic acid are dissolved in 1.5 ml THF and at room temperature 0.04 g (0.16 mmol) 2-ethoxy-1-ethoxycarbonyl-1.2-dihydroquinoline (EEDQ) are added. After 30 min, 0.029 g (0.16 mmol) of 3-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamine is added and the mixture is stirred for 12 h at 40° C. Then it is concentrated by evaporation i.vac. And purified by chromatography through RP material (Microsorb C18 Varian; eluant: water/acetonitrile/trifluoroacetic acid=90:10:0.1=>0:100:0.1).

Workup

  1. additionare added
  2. concentrationThen it is concentrated by evaporation i.vac
  3. customAnd purified by chromatography through RP material (Microsorb C18 Varian; eluant: water/acetonitrile/trifluoroacetic acid=90:10:0.1=>0:100:0.1)

Sources & evidence

ORD record
ord-b9807cb7f4374c5ba6eb6d040cf90024
Source dataset
uspto-grants-2015_06
Patent number
US09062034B2

Reaction notes

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