P-Anisidine → HCID 67373930, compound

HRID 1677007Notes

Reaction equation

HRID 1677007 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][NH:5][S:6]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([Br:18])[CH:16]=2)[N:11]([S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])[C:10]=1[C:28]([O:30][CH2:31][CH3:32])=[O:29])(=[O:8])=[O:7].C(N(CC)CC)C.Cl[C:41](Cl)([O:43]C(=O)OC(Cl)(Cl)Cl)Cl.[CH3:52][O:53][C:54]1[CH:60]=[CH:59][C:57]([NH2:58])=[CH:56][CH:55]=1>C1COCC1.CCOC(C)=O>[Br:18][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[N:11]([S:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:21])=[O:20])[C:10]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:9]2[S:6]([NH:5][CH2:4][CH2:3][NH:2][C:41]([NH:58][C:57]1[CH:59]=[CH:60][C:54]([O:53][CH3:52])=[CH:55][CH:56]=1)=[O:43])(=[O:8])=[O:7]

Participants

7

Reactant 4

HCID 7732P-AnisidineHCID 8471TriethylamineHCID 94429TriphosgeneHCID 67373781HCID 67373781, compound

Product 1

HCID 67373930HCID 67373930, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of the material from Step A above (25 mg) was dissolved in 1 mL of THF and cooled to 0° C. Triethylamine (25 μL) was added, followed by 4 mg of triphosgene. The reaction stirred for 5 minutes at 0° C., then 5 minutes at room temperature and then was recooled to 0° C. and stirred for 5 minutes more. A solution of 4-methoxyaniline in 1 mL of THF was added slowly. The reaction was stirred for 40 minutes, diluted with EtOAc and washed with 10% citric acid solution, saturated NaHCO3 and brine. The solution was dried (Na2SO4) and concentrated in vacuo to give the titled product.

Workup

  1. custom5 minutes
  2. customat room temperature
  3. customwas recooled to 0° C.
  4. stirringstirred for 5 minutes more
  5. stirringThe reaction was stirred for 40 minutes
  6. washwashed with 10% citric acid solution, saturated NaHCO3 and brine
  7. dry with materialThe solution was dried (Na2SO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-329abdfc47e148929dfa89f6f78c96cf
Source dataset
uspto-grants-2011_08
Patent number
US08008295B2

Reaction notes

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