2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → HCID 178453531, compound

HRID 578682Notes

Reaction equation

HRID 578682 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C:9]([OH:11])=O)[NH:7][N:8]=2)[CH2:3][CH2:2]1.CCOC1N(C(OCC)=O)C2C(=CC=CC=2)C=C1.[C:30]([O:34][C:35](=[O:48])[NH:36][CH:37]([C:41]1[CH:46]=[CH:45][CH:44]=[C:43]([NH2:47])[CH:42]=1)[CH2:38][CH2:39][OH:40])([CH3:33])([CH3:32])[CH3:31]>C1COCC1>[C:30]([O:34][C:35](=[O:48])[NH:36][CH:37]([C:41]1[CH:46]=[CH:45][CH:44]=[C:43]([NH:47][C:9]([C:6]2[NH:7][N:8]=[C:4]([CH:1]3[CH2:2][CH2:3]3)[CH:5]=2)=[O:11])[CH:42]=1)[CH2:38][CH2:39][OH:40])([CH3:33])([CH3:31])[CH3:32]

Participants

5

Reactant 3

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 66763679HCID 66763679, compoundHCID 178524106HCID 178524106, compound

Product 1

HCID 178453531HCID 178453531, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

529 mg (3.4 mmol) 5-Cyclopropyl-2H-pyrazole-3-carboxylic acid were suspended in 9 ml THF and 834 mg (3.4 mmol) EEDQ were added. The mixture was stirred for 10 min at room temperature and subsequently 900 mg (3.4 mmol) [1-(3-Amino-phenyl)-3-hydroxy-propyl]-carbamic acid tert-butyl ester dissolved in 9 ml THF were added. The mixture was stirred overnight at room temperature, evaporated to dryness. The residue was dissolved in ethyl acetate and washed with 1 N NaOH, 10% citric acid and brine. The organic layer was dried over Na2SO4 and evaporated to dryness. 1.37 g, clear oil.

Workup

  1. additionwere added
  2. stirringThe mixture was stirred overnight at room temperature
  3. customevaporated to dryness
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with 1 N NaOH, 10% citric acid and brine
  6. dry with materialThe organic layer was dried over Na2SO4
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-073a8c12cb0f4203a64d1889f1a9587d
Source dataset
uspto-grants-2015_05
Patent number
US09040560B2

Reaction notes

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