Tetrahydrofuran → HCID 59255313, compound

HRID 640427Notes

Reaction equation

HRID 640427 reaction equation
[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8](Cl)=[N:9][OH:10])[CH:2]=1.O1CCCC1.[C:23]([C:25]1[C:26]([NH2:32])=[N:27][C:28]([NH2:31])=[CH:29][CH:30]=1)#[CH:24].C(N(CC)CC)C>O>[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]2[CH:24]=[C:23]([C:25]3[C:26]([NH2:32])=[N:27][C:28]([NH2:31])=[CH:29][CH:30]=3)[O:10][N:9]=2)[CH:2]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 552816763-Ethynylpyridine-2,6-diamineHCID 72262885Biphenyl-3-yl-acetohydroximoyl chloride

Product 1

HCID 59255313HCID 59255313, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of biphenyl-3-yl-acetohydroximoyl chloride (60 mg) described in Manufacturing Example 85-1-3 and tetrahydrofuran (3 mL) were added 3-ethynyl-pyridin-2,6-diamine (15 mg, 0.11 mmol) described in Manufacturing Example 13-1-3 and triethylamine (94 μL, 0.68 mmol), which was stirred for 2 hours at room temperature. Water was added to the reaction mixture at the same temperature, which was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and was concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate) to obtain the title compound in a crude product. Then, the residue was purified by reverse-phase high performance liquid chromatography (using an acetonitrile-water mobile phase containing 0.1% trifluoroacetic acid) to obtain the title compound (32 mg, 62%) as a trifluoroacetic acid salt.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. concentrationwas concentrated under a reduced pressure
  4. customThe residue was purified by NH silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-5a1ed780b43e4214b3b64cf9cdf72d67
Source dataset
uspto-grants-2010_04
Patent number
US07691882B2

Reaction notes

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