Tetrahydrofuran → HCID 59255143, compound

HRID 1691373Notes

Reaction equation

HRID 1691373 reaction equation
[C:1]([C:3]1[C:4]([NH2:10])=[N:5][C:6]([NH2:9])=[CH:7][CH:8]=1)#[CH:2].C([C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25](Cl)=NO)=[C:20]([S:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)C=1)C1C=CC=CC=1.[CH2:36]([N:38](CC)CC)[CH3:37].[O:43]1CCCC1>>[CH2:20]([S:29][C:30]1[CH:31]=[CH:32][C:33]([CH2:37][C:36]2[CH:2]=[C:1]([C:3]3[C:4]([NH2:10])=[N:5][C:6]([NH2:9])=[CH:7][CH:8]=3)[O:43][N:38]=2)=[CH:34][CH:35]=1)[C:21]1[CH:22]=[CH:23][CH:18]=[CH:25][CH:24]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 552816763-Ethynylpyridine-2,6-diamineHCID 86612461(4-Benzylphenylsulfanyl-phenyl)acetohydroximoyl chloride

Product 1

HCID 59255143HCID 59255143, compoundYield 55%

Procedure

To a tetrahydrofuran (3 mL) solution of 3-ethynyl-pyridine-2,6-diamine (50 mg, 0.376 mmol) described in Manufacturing Example 13-1-3 and (4-benzylphenylsulfanyl-phenyl)acetohydroximoyl chloride (176 mg, 0.602 mmol) described in Manufacturing Example 205-1-5 was added triethylamine (131 μL, 0.94 mmol), which was stirred for 2 hours at room temperature. This mixture was partitioned into ethyl acetate and water. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:1, then ethyl acetate) to obtain the title compound (80 mg, 55%).

Workup

  1. customThis mixture was partitioned into ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with water and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under a reduced pressure
  7. customthe residue was purified by NH silica gel column chromatography (ethyl acetate

Sources & evidence

ORD record
ord-4d8f98349097414b9596547b910b59e1
Source dataset
uspto-grants-2012_04
Patent number
US08153662B2

Reaction notes

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