Triethylamine → HCID 20799538, compound

HRID 38166Notes

Reaction equation

HRID 38166 reaction equation
[O:1]=[C:2]1[N:11]([C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19]([NH:21][S:22]([C:25]3[S:26][C:27]([N+:30]([O-])=O)=[CH:28][CH:29]=3)(=[O:24])=[O:23])=[O:20])=[CH:14][CH:13]=2)[C:10](=[O:33])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.C(N(CC)CC)C>CO.[Pd]>[NH2:30][C:27]1[S:26][C:25]([S:22]([NH:21][C:19]([NH:18][C:15]2[CH:16]=[CH:17][C:12]([N:11]3[C:10](=[O:33])[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[NH:3][C:2]3=[O:1])=[CH:13][CH:14]=2)=[O:20])(=[O:23])=[O:24])=[CH:29][CH:28]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 22064367n-[4-(2,4-Dioxo(1,3-dihydroquinazolin-3-yl))phenyl]{[(5-nitro(2-thienyl))sulfonyl]amino}carboxamide

Product 1

HCID 20799538HCID 20799538, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-[4-(2,4-dioxo(1,3-dihydroquinazolin-3-yl))phenyl]{[(5-nitro(2-thienyl))sulfonyl]amino}carboxamide (from Example 1148) (20 mg, 0.041 mmol) in methanol (1.5 mL) and triethylamine (11 μL, 0.08 mmol) was added 10% Pd/C (5 mg, 0.005 mmol) under argon. The reaction mixture was hydrogenated under 1 atm H2 for 3 hr, filtered, concentrated and HPLC purified to give the aniline (6 mg, 33%). ES-MS (M+H)+=458.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customHPLC purified

Sources & evidence

ORD record
ord-23b6907dece145e69015d3af6a81d723
Source dataset
uspto-grants-2013_09
Patent number
US08524721B2

Reaction notes

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