Diisopropylethylamine → HCID 23599501, compound

HRID 1350886Notes

Reaction equation

HRID 1350886 reaction equation
Cl.Cl.[N:3]12[CH2:10][CH2:9][CH:6]([CH2:7][CH2:8]1)[C@H:5]([NH2:11])[CH2:4]2.[Br:12][C:13]1[S:17][C:16]([C:18](O)=[O:19])=[CH:15][CH:14]=1.O.ON1C2C=CC=CC=2N=N1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[N:3]12[CH2:10][CH2:9][CH:6]([CH2:7][CH2:8]1)[C@H:5]([NH:11][C:18]([C:16]1[S:17][C:13]([Br:12])=[CH:14][CH:15]=1)=[O:19])[CH2:4]2

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 3491155-Bromothiophene-2-carboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27960291-Hydroxybenzotriazole hydrateHCID 12494973(3S)-1-azabicyclo[2.2.2]octan-3-amine dihydrochloride

Product 1

HCID 23599501HCID 23599501, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (S)-N-1-azabicyclo[2.2.2]oct-3-ylamine dihydrochloride (1.9 g), 5-bromothiophene-2-carboxylic acid (1.97 g), 1-hydroxybenzotriazole hydrate (1.28 g), O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium tetrafluoroborate (3.06 g), and N,N-diisopropylethylamine (8.3 mL) in N,N-dimethylformamide (20 mL) was stirred at room temperature overnight. The solution was evaporated, and the residue was partitioned between aqueous sodium hydroxide and chloroform. The chloroform layer was dried (Mg2SO4), filtered, and evaporated. The residue was purified by flash chromatography on silica gel and eluted with 5%–20% 3.5M methanolic ammonia/chloroform mixtures. Evaporation of solvent gave white solid (3 g); MS (ES+) 315, 317 (MH+).

Workup

  1. customThe solution was evaporated
  2. customthe residue was partitioned between aqueous sodium hydroxide and chloroform
  3. dry with materialThe chloroform layer was dried (Mg2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel
  7. washeluted with 5%–20% 3.5M methanolic ammonia/chloroform mixtures
  8. customEvaporation of solvent

Sources & evidence

ORD record
ord-4c2a0f11c8104241ab72836ba07e82da
Source dataset
uspto-grants-2007_05
Patent number
US07214688B2

Reaction notes

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