HCID 68697948, compound → HCID 68694214, compound

HRID 2235159Notes

Reaction equation

HRID 2235159 reaction equation
C(OC([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18](=[O:31])[NH:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:22][CH:21]=3)[CH:16]=2)[CH2:11][CH2:10][CH2:9]1)=O)(C)(C)C>FC(F)(F)C(O)=O>[CH2:29]([O:28][C:26](=[O:27])[C:23]1[CH:22]=[CH:21][C:20]([NH:19][C:18]([C:15]2[CH:16]=[C:17]3[C:12]([CH2:11][CH2:10][CH2:9][NH:8]3)=[CH:13][CH:14]=2)=[O:31])=[CH:25][CH:24]=1)[CH3:30]

Participants

3

Reactant 1

HCID 68697948HCID 68697948, compound

Product 1

HCID 68694214HCID 68694214, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 7-(4-ethoxycarbonyl-phenylcarbamoyl)-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester (1.1 g, 2.5 mmol) in trifluoroacetic acid (5 ml) was stirred at room temperature for 2 hours. The solvent was then removed and the residue redissolved in dichloromethane and washed with saturated sodium hydrogencarbonate. The organic layer was dried with Na2SO4 and evaporated. The residue was purified by flash chromatography (heptane/ethyl acetate gradient) to yield 4-[(1,2,3,4-tetrahydro-quinoline-7-carbonyl)-amino]-benzoic acid ethyl ester as a white solid, 790 mg (97%). MS (ISP): m/e=325.4 (M+H+.); δH (300 MHz; CDCl3) 8.59 (1H, s), 7.98 (2H, d), 7.77 (1H, s), 7.69 (2H, d), 7.48 (1H, d), 7.09 (1H, d), 4.37 (2H, q), 3.44 (2H, m), 2.79 (2H, t), 2.08 (2H, m), 1.40 (3H, t).

Workup

  1. customThe solvent was then removed
  2. dissolutionthe residue redissolved in dichloromethane
  3. washwashed with saturated sodium hydrogencarbonate
  4. dry with materialThe organic layer was dried with Na2SO4
  5. customevaporated
  6. customThe residue was purified by flash chromatography (heptane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-7fd9fb8fa35a4070976e6993ff1706b7
Source dataset
uspto-grants-2010_05
Patent number
US07713996B2

Reaction notes

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