HCID 66671931, compound → HCID 178486759, compound

HRID 523883Notes

Reaction equation

HRID 523883 reaction equation
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[C:28]([N+:29]([O-])=O)=[CH:27][C:10]([O:11][CH2:12][C:13]2([NH:16][C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[CH2:15][CH2:14]2)=[C:9]([O:32][CH3:33])[CH:8]=1)=[O:6]>CC(O)=O.CCOC(C)=O.[Fe]>[OH:6][C:5]1[C:7]2[C:28](=[CH:27][C:10]([O:11][CH2:12][C:13]3([NH:16][C:17]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[O:18])[CH2:14][CH2:15]3)=[C:9]([O:32][CH3:33])[CH:8]=2)[N:29]=[CH:3][CH:4]=1

Participants

5

Reactant 1

HCID 66671931HCID 66671931, compound

Product 1

HCID 178486759HCID 178486759, compoundYield 95.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of the compound of Example 3 (1.5 g, 3.2 mmol) and powder iron (1.8 g, 32 mmol) in AcOH (15 mL) was stirred a 80° C. for 2 h. The reaction mixture was cooled at room temperature, diluted with AcOEt (150 mL), filtered and washed with 50 ml of AcOEt. The filtration liquors were combined, washed with water (2×100 mL) and an NaHCO3 saturated solution (2×100 mL), dried and evaporated to give 1-[(4-hydroxy-6-methoxyquinolin-7-yloxy)methyl]-N-benzyloxycarbonyl-1-aminocyclopropane (1.2 g, yield: 95%) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled at room temperature
  2. filtrationfiltered
  3. washwashed with 50 ml of AcOEt
  4. filtrationThe filtration liquors
  5. washwashed with water (2×100 mL)
  6. dry with materialan NaHCO3 saturated solution (2×100 mL), dried
  7. customevaporated

Sources & evidence

ORD record
ord-652aa62ede9745c787b86758d9dfb052
Source dataset
uspto-grants-2016_05
Patent number
US09340508B2

Reaction notes

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