3-[(2S)-oxiran-2-yl]pyridine → HCID 178526826, compound

HRID 1819446Notes

Reaction equation

HRID 1819446 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([CH2:8][NH:9][C:10]2[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][N:13]=[C:12]([NH:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[O:27][C:28]([F:31])([F:30])[F:29])[N:11]=2)[CH2:4][CH2:3]1.[O:32]1[CH2:34][C@@H:33]1[C:35]1[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=1.Cl([O-])(=O)(=O)=O.[Li+]>CC#N>[N+:16]([C:15]1[C:10]([NH:9][CH2:8][C@H:5]2[CH2:4][CH2:3][C@H:2]([NH:1][CH2:34][C@H:33]([C:35]3[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=3)[OH:32])[CH2:7][CH2:6]2)=[N:11][C:12]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[O:27][C:28]([F:30])([F:31])[F:29])=[N:13][CH:14]=1)([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 133195603-[(2S)-oxiran-2-yl]pyridineHCID 23665649Lithium perchlorateHCID 178511544HCID 178511544, compound

Product 1

HCID 178526826HCID 178526826, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of N4-[(trans-4-aminocyclohexyl)methyl]-5-nitro-N2-[2-(trifluoromethoxy)benzyl]pyrimidine-2,4-diamine (124 mg, 0.28 mmol), (S)-3-oxiranyl-pyridine (34 mg, 0.28 mmol) and lithium perchlorate (60 mg, 0.56 mmol) in CH3CN was heated to 100° C. in a sealed tube and stirred for 1 h. The reaction mixture was concentrated and diluted with ethyl acetate. The solution was then treated with 1M Na2CO3 and the organic phase was separated. The aqueous phase was re-extracted with ethyl acetate (×2). The combined organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel prep TLC using 10:1:0.05 CH2Cl2:MeOH:NH4OH as an eluent to afford 15 mg of the title compound as an off-white solid (10%), m/z 562.7 [M+1]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with ethyl acetate
  3. additionThe solution was then treated with 1M Na2CO3
  4. customthe organic phase was separated
  5. extractionThe aqueous phase was re-extracted with ethyl acetate (×2)
  6. dry with materialThe combined organic phase was dried over Na2SO4
  7. concentrationconcentrated
  8. customThe resulting residue was purified by silica gel prep TLC

Sources & evidence

ORD record
ord-38e50110a3e7464facdae6e591faf286
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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