Ammonia → HCID 178466941, compound

HRID 1295457Notes

Reaction equation

HRID 1295457 reaction equation
[CH2:1]([O:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH:14]=[C:15]3[S:19][C:18](=S)[NH:17][C:16]3=[O:21])[CH:12]=2)[N:7]=[C:6]([NH:22][C:23](=[O:25])[CH3:24])[CH:5]=1)[CH3:2].C([N:29](C(C)C)CC)(C)C.CI.N.CO>C(#N)C>[NH2:29][C:18]1[S:19][C:15](=[CH:14][C:11]2[CH:12]=[C:13]3[C:8](=[CH:9][CH:10]=2)[N:7]=[C:6]([NH:22][C:23](=[O:25])[CH3:24])[CH:5]=[C:4]3[O:3][CH2:1][CH3:2])[C:16](=[O:21])[N:17]=1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 887MethanolHCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 178466942HCID 178466942, compound

Product 1

HCID 178466941HCID 178466941, compoundYield 663%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of N-[4-ethoxy-6-(4-oxo-2-thioxo-thiazolidin-5-ylidenemethyl)-quinolin-2-yl]-acetamide (example 6a, 80 mg, 0.21 mmol) in acetonitrile (3 ml) was reacted with diisopropylethyl amine (0.40 ml, 2.2 mmol) and methyl iodide (0.30 ml, 4.6 mmol) at rt for 30 min. The mixture was concentrated to dryness and the residue suspended in DMF (0.5 ml). A solution of ammonia in methanol (7N, 5 ml, 35 mmol) was added at rt, and the mixture was stirred at rt for 24 h. The mixture was concentrated to dryness and the solid was triturated with water. The precipitate was collected by suction filtration, successively washed with water and ether, and then air dried to afford the product as a light brown solid (50 mg, 663%). LC-MS m/e 357 (MH+).

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. concentrationThe mixture was concentrated to dryness
  3. customthe solid was triturated with water
  4. filtrationThe precipitate was collected by suction filtration
  5. washsuccessively washed with water and ether
  6. customair dried

Sources & evidence

ORD record
ord-73e7ce8003af42d6a5f1cfb3830945b5
Source dataset
uspto-grants-2007_07
Patent number
US07241893B2

Reaction notes

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