HCID 86713594, compound → HCID 86713593, compound

HRID 2404052Notes

Reaction equation

HRID 2404052 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[C:13]1[C:14](=[O:35])[N:15]([CH3:34])[C:16]2[C:21]([CH:22]=1)=[CH:20][N:19]=[C:18]([NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[N+:30]([O-])=O)[C:17]=2[CH3:33]>C(OCC)(=O)C>[NH2:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[NH:23][C:18]1[C:17]([CH3:33])=[C:16]2[C:21]([CH:22]=[C:13]([C:3]3[C:2]([Cl:1])=[C:7]([O:8][CH3:9])[CH:6]=[C:5]([O:10][CH3:11])[C:4]=3[Cl:12])[C:14](=[O:35])[N:15]2[CH3:34])=[CH:20][N:19]=1

Participants

3

Reactant 1

HCID 86713594HCID 86713594, compound

Product 1

HCID 86713593HCID 86713593, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-(2,6-dichloro-3,5-dimethoxyphenyl)-1,8-dimethyl-7-(2-nitrophenylamino)-1,6-naphthyridin-2(1H)-one (100 mg, 0.2 mmol) in ethyl acetate (20 mL) was added stannous chloride (150 mg, 0.8 mmol), and the mixture was stirred at 80° C. for 1 h. LCMS monitored the reaction was completed. The solid was filtered off, and the filtrate was concentrated. The residue was purified by Prep-HPLC to get the title compound (38.6 mg, 41%) as a yellow solid. MS (ES+) C24H22Cl2N4O3 requires: 484, 486. found: 485, 487 [M+H]+; 1H-NMR (500 MHz, DMSO-d6) δ ppm 8.24 (s, 1H), 7.76 (s, 1H), 7.67 (s, 1H), 7.03 (d, 1H, J=7.5 Hz), 6.97 (s, 1H), 6.92-6.89 (m, 1H), 6.75-6.73 (m, 1H), 6.57-6.54 (m, 1H), 4.77 (s, 2H), 3.95 (s, 6H), 3.66 (s, 3H), 2.43 (s, 3H).

Workup

  1. filtrationThe solid was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by Prep-HPLC

Sources & evidence

ORD record
ord-2a4582789002446bb5d2f4886cafee5f
Source dataset
uspto-grants-2014_08
Patent number
US08802697B2

Reaction notes

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