p-Anisoyl chloride → HCID 11351693, compound

HRID 1726460Notes

Reaction equation

HRID 1726460 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][S:10]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([NH2:23])=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[CH:5][CH:4]=1.[CH3:24][O:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1.CCN(CC)CC>C(Cl)Cl>[CH3:24][O:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([NH:23][C:16]2[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:13]([S:10](=[O:12])(=[O:11])[NH:9][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)=[CH:14][CH:15]=2)=[O:31])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 16105845HCID 16105845, compound

Product 1

HCID 11351693HCID 11351693, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of naphthalenyl amine (10) (65 mg, 0.2 mmol) in CH2Cl2 (5 mL) was added p-methoxybenzoyl chloride (45 μL, 0.24 mmol) and Et3N (50 μL, 0.4 mmol). The resultant solution was stirred at 25° C. overnight. The solvent was removed in vacuo and the residue was purified using HPLC to give the title compound (30 mg) as pale yellow solid. 1H NMR (300 MHz, MeOD) δ 8.73 (d, 1H), 8.08 (m, 4H), 7.70 (m, 3H), 7.10 (d, 2H), 6.90 (d, 2H), 6.70 (d, 2H), 3.84 (s, 3H), 3.60 (s, 3H); LC/MS m/z 463 (M+H)+.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified

Sources & evidence

ORD record
ord-55e398716069431abac45ac648d22884
Source dataset
uspto-grants-2009_02
Patent number
US07491827B2

Reaction notes

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