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

HRID 474446Notes

Reaction equation

HRID 474446 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-7587a64cb3b3452b8820079a1a2a718b
Source dataset
uspto-grants-2014_01
Patent number
US08637532B2

Reaction notes

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