1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-(N-(tert-butoxycarbonyl)-L-alanyl)oxy-7-methyl-3-(3-trifluoromethylphenyl)-5,6,7,8-tetrahydrocinnoline

HRID 229722

Reaction equation

HRID 229722 reaction equation
[CH3:1][CH:2]1[CH2:11][C:10]2[N:9]=[N:8][C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=3)=[CH:6][C:5]=2[CH:4]([OH:22])[CH2:3]1.C(N=C=NCCCN(C)C)C.[C:34]([O:38][C:39]([NH:41][C@H:42]([C:44](O)=[O:45])[CH3:43])=[O:40])([CH3:37])([CH3:36])[CH3:35]>O1CCCC1.ClCCl>[C:34]([O:38][C:39]([NH:41][C@H:42]([C:44]([O:22][CH:4]1[CH2:3][CH:2]([CH3:1])[CH2:11][C:10]2[N:9]=[N:8][C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=3)=[CH:6][C:5]1=2)=[O:45])[CH3:43])=[O:40])([CH3:36])([CH3:37])[CH3:35]

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 85082Tert-butoxycarbonylalanineHCID 99725287-Methyl-3-(3-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydrocinnolin-5-ol

Product 1

HCID 688445095-(N-(tert-butoxycarbonyl)-L-alanyl)oxy-7-methyl-3-(3-trifluoromethylphenyl)-5,6,7,8-tetrahydrocinnoline

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

7-Methyl-3-(3-trifluoromethylphenyl)-5,6,7,8-tetrahydrocinnolin-5-ol (10 mg, 0.03 mmol) obtained in Example 6 was dissolved in a mixed solvent of tetrahydrofuran and dichloromethane (0.5 mL. 0.5 mL), followed by adding N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide (9 mg, 0.045 mmol), N,N-dimethylaminopyridine (catalytic amount) and N-(tert-butoxycarbonyl)-L-alanine (9 mg, 0.045 mmol) and stirring at room temperature over night. After completion of the reaction, the reaction liquid was concentrated and thus obtained residue was purified using silica gel column chromatography (hexane/ethyl acetate=1/1) to obtain an objective compound.

Workup

  1. customAfter completion of the reaction
  2. customthe reaction liquid
  3. concentrationwas concentrated
  4. customthus obtained residue was purified
  5. customto obtain an objective compound

Sources & evidence

ORD record
ord-17dc1c9c39fe4caa8b43c4efcbfec233
Source dataset
uspto-grants-2009_07
Patent number
US07563893B2

Linked notes

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