Triethylamine → HCID 90204028, compound

HRID 1480181Notes

Reaction equation

HRID 1480181 reaction equation
[CH:1]1([C:4]2[C:5]([O:13][CH2:14][C:15]([F:18])([F:17])[F:16])=[CH:6][C:7]([C:10]([OH:12])=O)=[N:8][CH:9]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH2:48]([O:55][CH2:56][C:57]([C:60]1[N:64]=[C:63]([CH3:65])[O:62][N:61]=1)([NH2:59])[CH3:58])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>CN(C=O)C>[CH:1]1([C:4]2[C:5]([O:13][CH2:14][C:15]([F:18])([F:17])[F:16])=[CH:6][C:7]([C:10]([NH:59][C:57]([C:60]3[N:64]=[C:63]([CH3:65])[O:62][N:61]=3)([CH3:58])[CH2:56][O:55][CH2:48][C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)=[O:12])=[N:8][CH:9]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 902036745-Cyclopropyl-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acidHCID 90204098HCID 90204098, compound

Product 1

HCID 90204028HCID 90204028, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-Cyclopropyl-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid (example 48c, 0.58 g, 2.22 mmol) in dry DMF (10 ml) was added triethylamine (270 mg, 371 μl, 2.66 mmol) and TBTU (713 mg, 2.22 mmol). The reaction mixture was stirred at room temperature for 30 minutes followed by addition of 1-(benzyloxy)-2-(5-methyl-1,2,4-oxadiazol-3-yl)propan-2-amine (example 112d, 577 mg, 2.33 mmole) and the reaction was then stirred at room temperature overnight. DMF was removed in vacuo and the residue was dissolved in ethyl acetate. The organic phase was extracted with a 2M aqueous solution of sodium carbonate and the organic phase was collected. The organic phase was dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a heptane/ethyl acetate gradient to yield the title compound (805 mg, 74%) as a light yellow oil. MS (ESI, m/z): 491.5 (M+H+).

Workup

  1. stirringthe reaction was then stirred at room temperature overnight
  2. customDMF was removed in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. extractionThe organic phase was extracted with a 2M aqueous solution of sodium carbonate
  5. customthe organic phase was collected
  6. dry with materialThe organic phase was dried over sodium sulfate
  7. customevaporated down to dryness
  8. customThe crude material was purified by flash chromatography on silica eluting with a heptane/ethyl acetate gradient

Sources & evidence

ORD record
ord-9fa84c9189b549aaa12f3685f82d6099
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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