Ammonia → HCID 22288477, compound

HRID 968219Notes

Reaction equation

HRID 968219 reaction equation
N.[Cl:2][C:3]1[C:8]([N+:9]([O-:11])=[O:10])=[C:7](Cl)[N:6]=[C:5]([S:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:4]=1.C([N:24](C(C)C)CC)(C)C>C1COCC1>[Cl:2][C:3]1[N:4]=[C:5]([S:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:6]=[C:7]([NH2:24])[C:8]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 22288487HCID 22288487, compound

Product 1

HCID 22288477HCID 22288477, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ammonia solution (14 ml, 0.5 M in dioxane) was added dropwise to a solution of the product of example 2, step (c) (2.0 g) and diisopropylethylamine (3.31 ml) in THF (100 ml) over a 1 h period at RT. After stirring for a further 1 h the reaction was concentrated in vacuo onto silica and purified by column chromatography using 9:1 then 4:1 isohexane/ethyl acetate as eluent to yield the subtitled product as a yellow solid (980 mg, 52%).

Workup

  1. concentrationwas concentrated in vacuo onto silica
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-4b7deafe37c54d05b3b6e621d69e3328
Source dataset
uspto-grants-2005_10
Patent number
US06958344B2

Reaction notes

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