Butylamine → HCID 67332077, compound

HRID 1896756Notes

Reaction equation

HRID 1896756 reaction equation
[C:1]1([CH3:19])[CH:6]=[CH:5][C:4]([C:7]2[O:8][C:9]3[CH:15]=[CH:14][C:13]([C:16]([OH:18])=O)=[CH:12][C:10]=3[N:11]=2)=[CH:3][CH:2]=1.CN(C(O[N:28]1N=N[C:30]2[CH:31]=[CH:32]C=N[C:29]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.C(N)CCC>CN(C)C=O.C(OCC)(=O)C>[CH2:29]([NH:28][C:16]([C:13]1[CH:14]=[CH:15][C:9]2[O:8][C:7]([C:4]3[CH:3]=[CH:2][C:1]([CH3:19])=[CH:6][CH:5]=3)=[N:11][C:10]=2[CH:12]=1)=[O:18])[CH2:30][CH2:31][CH3:32]

Participants

7

Reactant 4

HCID 8007ButylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 115578892-p-tolylbenzo[d]oxazole-5-carboxylic acid

Product 1

HCID 67332077HCID 67332077, compoundYield 21.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 2-p-tolylbenzo[d]oxazole-5-carboxylic acid (100 mg, 0.39 mmol) in dry dimethylformamide (10 mL) was added HATU (165 mg, 0.44 mmol) and diisopropylethylamine (206 μL, 1.18 mmol). The mixture was then stirred at room temperature for 10 min. Butan-1-amine (43 μL, 0.44 mmol) was then added and the resulting mixture was stirred at room temperature for 16 h. Ethyl acetate was added and the organic layer was washed three times with water. The combined organic layers were dried over anhydrous MgSO4 and evaporated. The resulting solid was purified by column chromatography eluting with ethyl acetate/hexanes 40:60 v/v to afford 26 mg (11%) of the title compound (LCMS RT=6.81 min, MH+ 309.1)

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 16 h
  2. washthe organic layer was washed three times with water
  3. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  4. customevaporated
  5. customThe resulting solid was purified by column chromatography
  6. washeluting with ethyl acetate/hexanes 40:60 v/v

Sources & evidence

ORD record
ord-6df9a07b07b241e19bb6543f20a69709
Source dataset
uspto-grants-2013_08
Patent number
US08518980B2

Reaction notes

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