Hydrochloric Acid → HCID 86643682, compound

HRID 1614936Notes

Reaction equation

HRID 1614936 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][NH:6][C:7]1[C:12]([Cl:13])=[CH:11][N:10]=[C:9]([Cl:14])[N:8]=1.Cl.C(N(CC)CC)C.[N+:26]([C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=1)[C:32](Cl)=[O:33])([O-:28])=[O:27]>C1COCC1>[Cl:14][C:9]1[N:8]=[C:7]([NH:6][CH2:5][C:4]2[CH:3]=[C:2]([NH:1][C:32](=[O:33])[C:31]3[CH:35]=[CH:36][CH:37]=[C:29]([N+:26]([O-:28])=[O:27])[CH:30]=3)[CH:17]=[CH:16][CH:15]=2)[C:12]([Cl:13])=[CH:11][N:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 8495Benzoyl chloride, 3-nitro-HCID 58467912HCID 58467912, compound

Product 1

HCID 86643682HCID 86643682, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of N-(3-aminobenzyl)-2,5-dichloropyrimidin-4-amine.hydrogen chloride (0.10 g, 0.29 mmol) (prepared according to Example 3, step B) and triethylamine (0.16 mL, 1.2 mmol) in THF (3 mL) was added slowly 3-nitrobenzoyl chloride (54 mg, 0.29 mmol). The resulting mixture was stirred at rt for 2 hours and concentrated under vacuum. The residue was partitioned in EtOAc and water. The organic layer was dried over Na2SO4, filtered, and concentrated under vacuum to give the desired product as a yellow solid (90 mg, 70%). LCMS for C18H14Cl2N5O3 (M+H)+: m/z=418.0, 420.0.

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue was partitioned in EtOAc
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-37ae2d38467b41dcbe5ff62987b1f677
Source dataset
uspto-grants-2014_07
Patent number
US08765727B2

Reaction notes

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