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Tetrahydrofuran → 3-(3-(4-Benzyloxy-benzyl)-isoxazol-5-yl)-6-methoxymethyl-pyridin-2-ylamine

HRID 77843
Notes
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Reaction equation

HRID 77843 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16](Cl)=[N:17][OH:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.[C:25]([C:27]1[C:28]([NH2:36])=[N:29][C:30]([CH2:33][O:34][CH3:35])=[CH:31][CH:32]=1)#[CH:26].C(N(CC)CC)C>O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]2[CH:26]=[C:25]([C:27]3[C:28]([NH2:36])=[N:29][C:30]([CH2:33][O:34][CH3:35])=[CH:31][CH:32]=3)[O:18][N:17]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 592550943-Ethynyl-6-methoxymethyl-pyridin-2-ylamineHCID 722628734-Benzyloxy-phenyl-acetohydroximoyl chloride

Product 1

HCID 592554553-(3-(4-Benzyloxy-benzyl)-isoxazol-5-yl)-6-methoxymethyl-pyridin-2-ylamineYield 41.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of (4-benzyloxy-phenyl)-acetohydroximoyl chloride (19 mg, 0.069 mmol) described in Manufacturing Example 1-1-3 and tetrahydrofuran (1 mL) were added 3-ethynyl-6-methoxymethyl-pyridin-2-ylamine (8.6 mg, 0.053 mmol) described in Manufacturing Example 26-1-7 and triethylamine (15 μL, 0.11 mmol) at room temperature, which was stirred for 5.5 hours at room temperature. Water was added at room temperature to the reaction mixture, which was then extracted with ethyl acetate-tetrahydrofuran (3:2). The organic layer was washed with saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=2:3) to obtain the title compound (8.8 mg, 41%).

Workup

  1. extractionwas then extracted with ethyl acetate-tetrahydrofuran (3:2)
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. customthe solvent was evaporated under a reduced pressure
  4. customThe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=2:3)

Sources & evidence

ORD record
ord-d8ca385032f849f7803e2c33e188ddf5
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08841327B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes