Diisopropylethylamine → HCID 54036966, compound

HRID 2288934Notes

Reaction equation

HRID 2288934 reaction equation
F[P-](F)(F)(F)(F)F.[N:8]1([O:17]C(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[CH3:25][N:26]([CH2:34][C:35]1[CH:40]=[CH:39][C:38]([C:41]2[CH:46]=[CH:45][C:44]([C:47]#[N:48])=[CH:43][CH:42]=2)=[CH:37][CH:36]=1)[S:27]([CH2:30][C:31](O)=[O:32])(=[O:29])=[O:28].C(N(C(C)C)C(C)C)C.Cl.NO>CN(C)C=O>[OH:17][NH:8][C:31](=[O:32])[CH2:30][S:27]([N:26]([CH3:25])[CH2:34][C:35]1[CH:40]=[CH:39][C:38]([C:41]2[CH:42]=[CH:43][C:44]([C:47]#[N:48])=[CH:45][CH:46]=2)=[CH:37][CH:36]=1)(=[O:28])=[O:29]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 18702056HCID 18702056, compound

Product 1

HCID 54036966HCID 54036966, compoundYield 8.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

O-(7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU 263 mg, 0.72 mmol) was added to a solution of 2-({methyl[(4'-cyanobiphenyl-4-yl)methyl]amino}sulfonyl)acetic acid (185 mg, 0.48 mmol) and N-ethyl-N,N-diisopropylamine (0.08 ml, 0.48 mmol) in anhydrous dimethylformamide (3 ml) at ambient temperature under an atmosphere of nitrogen. After stirring for 20 minutes a solution of hydroxylamine hydrochloride (131 mg, 1.92 mmol) and N-ethyl-NN-diisopropylamine (0.33 ml, 1.92 mmol) in anhydrous dimethylformamide (1 ml) was added and the solution was stirred for a further 16 hours. The mixture was partitioned between aqueous phosphate buffer (at pH 7) and ethyl acetate. The organic layer was washed with water, dried (MgSO4) and the solvent evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (dichloromethane/methanol/aqueous ammonia 90:10:1 as eluent) to give the title compound as a colourless solid (14 mg).

Workup

  1. additionwas added
  2. customThe mixture was partitioned between aqueous phosphate buffer (at pH 7) and ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried (MgSO4)
  5. customthe solvent evaporated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (dichloromethane/methanol/aqueous ammonia 90:10:1 as eluent)

Sources & evidence

ORD record
ord-6c06b13d67a74a71a31f1177796b235c
Source dataset
uspto-grants-2000_07
Patent number
US06090852

Reaction notes

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