HCID 66815452, compound → HCID 43704708, compound

HRID 1944521Notes

Reaction equation

HRID 1944521 reaction equation
C(OC(=O)[NH:7][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>[NH2:7][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 66815452HCID 66815452, compound

Product 1

HCID 43704708HCID 43704708, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of [4-(quinolin-3-ylcarbamoyl)-phenyl]-carbamic acid tert-butyl ester (7.2 g, 19.8 mmol) in dichloromethane (70 mL), trifluoroacetic acid (70 mL) and water (7 mL) was stirred at ambient temperature for approximately 18 hours. The solvent was evaporated in vacuo, and the resultant residue was triturated in water (100 mL) and saturated aqueous sodium bicarbonate (100 mL). The product was collected by filtration, washed with water and dried in vacuo, to give a colorless solid, 4.36 g (84%). MS: m/z 264 (MH+). 1H NMR (DMSO-d6): δ 5.87 (br s, 2 H), 6.64 (d, 2 H), 7.55-7.67 (m, 2 H), 7.81 (d, 2 H), 7.94 (t, 2 H), 8.81 (d, J=2 Hz, 1 H), 9.14 (d, J=2 Hz, 1 H) and 10.22 (br s, 1 H).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe resultant residue was triturated in water (100 mL)
  3. filtrationThe product was collected by filtration
  4. washwashed with water
  5. customdried in vacuo
  6. customto give a colorless solid, 4.36 g (84%)

Sources & evidence

ORD record
ord-1a5e3a637dda4877ae31492694dfe289
Source dataset
uspto-grants-2013_03
Patent number
US08394828B2

Reaction notes

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