HCID 66815687, compound → HCID 59859876, compound

HRID 1944525Notes

Reaction equation

HRID 1944525 reaction equation
C(O[C:6](=O)[N:7](C)[C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:26])[NH:15][C:16]2[CH:17]=[N:18][C:19]3[C:24]([CH:25]=2)=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:10][CH:9]=1)(C)(C)C>ClCCl.FC(F)(F)C(O)=O.O>[CH3:6][NH:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]([NH:15][C:16]2[CH:17]=[N:18][C:19]3[C:24]([CH:25]=2)=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:26])=[CH:12][CH:13]=1

Participants

5

Reactant 1

HCID 66815687HCID 66815687, compound

Product 1

HCID 59859876HCID 59859876, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of methyl-[4-(quinolin-3-ylcarbamoyl)-phenyl]-carbamic acid tert-butyl ester (8.5 g, 22.5 mmol) in dichloromethane (100 ml), trifluoroacetic acid (100 mL) and water (10 mL) was stirred at room temperature for 6 hours. The solvent was evaporated in vacuo, and the residue was suspended in 1 N aqueous sodium hydroxide (200 mL). The product was collected by filtration, washed with water and dried in vacuo, to give a colorless solid, 5.4 g (87%). MS: m/z 278 (MH+). 1H NMR (DMSO-d6): 2.77 (d, 3 H), 6.44 (br d, 1 H), 6.63 (d, 2 H), 7.54-7.67 (m, 2 H), 7.89 (d, 2 H) superimposed on 7.95 (t, 2 H), 8.82 (d, 1 H), 9.16 (d, 1 H) and 10.26 (s, 1 H).

Workup

  1. customThe solvent was evaporated in vacuo
  2. filtrationThe product was collected by filtration
  3. washwashed with water
  4. customdried in vacuo
  5. customto give a colorless solid, 5.4 g (87%)

Sources & evidence

ORD record
ord-07eb629195f64f78b30548fa1d790a73
Source dataset
uspto-grants-2013_03
Patent number
US08394828B2

Reaction notes

Loading…